intermediates for the pur industry · 3 the key to producing high-end polyurethanes basf has a...
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Intermediates
Intermediates for the PUR IndustryTop properties for PUR
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BASFThe Chemical Company
BASF is the world’s leading chemical company: The Chemical Company. Its portfolio ranges from chemicals, plastics, performance products and crop protection products to oil and gas. We combine economic success, social responsibility and environmental protection. Through science and innovation we enable our customers in almost all industries to meet the current and future needs of society. Our products and system solutions contribute to conserving resources, ensuring healthy food and nutrition and helping to improve the quality of life. We have summed up this contribution in our corporate purpose: We create chemistry for a sustainable future.
Top intermediates supplierThe BASF Group’s Intermediates division develops, produces and markets a comprehensive portfolio of more than 600 intermediates around the world. The most important of the division’s product groups include amines, diols, polyalcohols, acids and specialties. Among other applications, intermediates are used as starting materials for coatings, plastics, pharmaceuticals, textile fibers, detergents and crop protectants. Innovative intermediates from BASF help to improve the properties of fi nal products and the effi ciency of production processes. The ISO 9001:2000-certifi ed Intermediates division operates plants at production sites in Europe, Asia, and the Americas.
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The key to producing high-end polyurethanes
BASF has a globally unique portfolio of chemical intermediates for the manufacture of outstandingly versatile polyurethane (PUR) materials, including an extensive range of high-perfor-mance catalysts, polyols, additives and solvents. In addition to a high level of supplier reliability through backward integration and global PUR expertise, BASF offers local presence and extensive customer services. The company also provides wide-ranging support in the development of innovative products and processes.
Comprehensive portfolio of PUR intermediates on pages 12-15
Catalysts (page 4) Polyols (page 5) Additives (page 9) Solvents (page 10)
Lupragen® catalysts Butanediol (BDO)
Polytetrahydrofuran (PolyTHF®)
Hexanediol (HDO)
Pentanediol (PDO)
Trimethylolpropane
(TMP)
Capromer™ polycaprolactons
Ethanolamines (EOA)
Methyldiethanolamine (MDEOA)
N4-Amine
Aminoethylethanol-amine (AEEA)
Isopropanolamine
Basionics™ antistatics
Dimethylformamide(DMF)
N,N-Dimethyl-acetamide (DMAC)
N-Methyl-2-pyrrolidone (NMP)
N-Ethyl-2-pyrrolidone(NEP)
Propylene carbonate(PC)
While rigid and semi-rigid PUR foams are used for insulation, dashboards and insulating board, fl exible foam is used for upholstering car seats, furniture and mattresses. You also fi nd PUR foam in the soles of shoes and in energy absorbing materials in the automotive industry. BASF products are appreciated in the production of thermoplastic polyurethanes (TPU) and PUR dispersions as well. Polycaprolactones available by the name of Capromer are exceptionally well suited to this application.
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Catalysts
LupragenBASF has more than 15 PUR amine catalysts in its product portfolio that make it a world leader in this segment. The company markets high-performance reaction accelerators under the Lupragen® brand, including extremely low-emission PUR catalysts.
As the world‘s leading chemical company BASF is offering excellent and consistent product quality, high supplier reliability, and worldwide product availability with dedicated production facilities in Europe and North America.
PUR catalysts are usually tertiary amines. They are required to facilitate the reaction of the main components isocyanate and polyol. Depending on the catalyst choice the polyurethane forming process can be controlled to favor the gelling or blowing reaction. This behavior leads to PUR material with the desired properties, depending on whether the final product is to be a rigid, semi-rigid or flexible foam (see pages 12/13).
BASF Lupragen catalysts offer the following advantages
One-stop product portfolio covering all desired application areas from rigid to flexible PUR foam
Availability of low-VOC catalysts addressing increasing environmental and health issues in end-consumer products
Excellent and consistent catalyst quality
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The mechanical properties of components made of glassfi ber-reinforced epoxy resins are determined by means of state-of-the-art testing equipment.
Butanediol (BDO)BASF is the world’s biggest producer of 1,4-butanediol (BDO)and its derivatives. BDO is a bifunctional alcohol that is very widely used in the chemical industry. The terminal OH in each of the –CH2OH groups of BDO can be reacted with numerous monofunctional and bifunctional compounds, for example to form polyesters with dicarboxylic acids, PUR with diisocyanates, and polycarbonates with phosgene. It is also used as a building block in the production of polyester polyols and polyether polyols.
BDO and its derivatives are used for producing engineering plastics, PUR, solvents, electronic chemicals and elastic fibers.
Main BDO reaction types in PUR chemistry:
BDO + dicarboxylic acids polyester polyols
BDO + alkylene oxides polyether polyols
BDO + diisocyanates PUR
Polyols
Polytetrahydrofuran (PolyTHF): PolyTHF® is one of the main soft segments for thermoplastic elastomers and crosslinked elastomers.
The hard segment of thermoplastic elastomers generally consists of chain extenders such as short-chain diols (e.g. 1,4-butanediol) and diamines (e.g. 1,2-propylenediamine). The amorphous soft segment (PolyTHF) not only imparts elasticity and low-temperature flexibility to the finished product but influences the chemical behavior as well. Careful adjustment of the soft segment fine-tunes the desired properties of the final application.
BASF is the global market leader in PolyTHF production and manufactures a wide range of PolyTHF molecular weights, including the standard molecular weights 650, 1,000 and 2,000; as well as special 250, technical grade, molecular weights.
PolyTHF is the ideal soft segment for PUR with:
Excellent dynamic mechanical properties across a wide temperature range
Exceptional low-temperature behavior
Superior hydrolytic stability
High moisture vapor transmission
Excellent abrasion resistance
High microbial resistance
The physical and chemical properties of PolyTHF give it advantages over competitive materials such as polyester polyols, due in particular to its superior hydrolytic stability and microbial resistance.
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Hexanediol (HDO) 1,6-Hexanediol (HDO) is a valuable specialty intermediate chemical with many applications. A linear diol containing two primary hydroxyl groups, HDO is a white, waxy solid at room temperature and melts easily to a clear liquid at temperatures above its melting range of 40 – 42 °C.
HDO is produced at our global Verbund sites in Ludwigshafen, Germany, and Freeport, Texas. Molten HDO and HDO flakes are the grades supplied.
HDO undergoes all reactions typical of primary alcohols.
HDO properties are of particular value in the manufacture of polyester polyols used in PUR elastomers, PUR dispersions, coatings and adhesives. Downstream applications of the above include protective and industrial coatings, microcellular PUR, cast elastomers, fibers, cosmetics, printing inks and many more. HDO can also be used as a chain extender.
HDO-based polyester polyols can be used as soft fibre in polymers and are characterized by
High resistance to hydrolysis
Good physical properties
Low glass transition temperature
Dry grip
Pure potential: 1,5-pentanediol (PDO) 1,5-Pentanediol (PDO) is a bifunctional alcohol used in the synthesis of innovative TPU, polyester resins, plasticizers, pharmaceuticals, crop protection agents and piperidine. Our high-quality PDO opens up new opportunities in the organic synthesis of products requiring a 5-carbon unit.
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Trimethylolpropane (TMP) Trimethylolpropane (TMP) is a major intermediate with a wide range of applications in the chemical industry, the main ones being PUR, polyester polyols, polyether polyols, binders and adhesives, synthetic lubricants, polyester and alkyd resin coatings.
TMP with its three primary alcohol groups is used as a three-functional crosslinking agent. It is a white solid at room temperature and easily melts to give a clear liquid at temperatures above its melting range of 58–60 °C.
TMP has a wide variety of applications, with a quaternary structure providing:
Superior hydrolytic stability
Weatherability
A good balance between hardness and flexibility
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Capromer polycaprolactones Capromer™ polycaprolactones are speciality polyols for high-performance PUR applications. Low-viscosity di- and trifunctional polyols are available as components for isocyanate-based formulation systems. Capromers offer outstanding low-temperature flexibility for thermoplastic elastomers used in technical applications and coatings. BASF’s Capromers are used where high hydrolytic stability is required together with good light-fastness. The polycaprolactones have a very low melting viscosity for easy processing of PUR elastomers. Capromer-based PUR dispersions are the best choice for any textile and leather application. For coatings applications the low viscosity facilitates high-solids systems or even solvent-free formulations. Such coatings offer excellent weatherability and chemical resistance.
Trifunctional Capromers have extraordinarily low viscosity and increase the resistance in any PU-based adhesives and coatings consistent reactivity.
The unique manufacturing process results in Capromers of unique quality with low catalyst levels for consistent reactivity of the PUR reaction in your process.
Capromers are available as standard grades and as premium grades with reduced acid value for even greater hydrolytic stability.
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Additives
Aminoethylethanol amine (AEEA) is used as a chain extender and cross-linker for PUR and affects polymer properties accordingly. The product’s bifunctionality is a requirement for its use in these areas. Both the hydroxy and the amine function react very well with isocyanates.
Methyldiethanolamine (MDEOA) is an amine-based polyol that is suitable for use as a PUR catalyst and as a special polyol in PUR synthesis. A double-action additive (catalyst and polyol), MDEOA is also a useful cross-linker and chain extender. BASF is the world’s only manufacturer with full backward integration covering all the raw materials contained in MDEOA.
Ethanolamines (EOA) are used in various PUR applications as chain extenders and cross-linkers. Mono-, di- and triethanolamine (MEOA, DEOA, TEOA) forms exist. DEOA and TEOA may be used as polyme-rization starters in polyol manufacture. The catalytic effect also provides a means of controlling the foaming rate and subse-quent curing. BASF offers a high level of supplier reliability as a European market leader with full backward integration into raw materials and plants in Germany, Asia and Belgium. The company also has an extensive product range with a variety of solutions and mixtures. Mono-, di- and triethanolamine (MEOA, DEOA, TEOA) are produced from synthesis of ethylene oxide and ammonia. In addition to pure grades and an array of mixtures and solutions, BASF supplies a mixture of TEOA and DEOA created especially for the PUR market and sold under the product name Triethanolamine S.
N4-Amine is making a name as a special catalyst in the flexible foam segment. The high amine content significantly reduces starting time. This property is an advantage when rapid foam injection is required.
IsopropanolaminesMonoisopropanolamine (MIPA), diisopropanolamine (DIPA) and triisopropanolamine (TIPA) are suitable as PUR additive.
In the manufacture of flexible foams, these products can be used in order to adjust parameters like tensile and tear strength and can aid in high-temperature resistance.
Basionics antistaticsBasionicsTM are outstanding new additives to provide antistatic properties to polyurethanes. Basionics antistatics may be applied to a wide range of PUR products, from low-density flexible foams, to microcellular materials, to compact PUR materials like cast elastomers or TPU. They allow a targeted selection in terms of conductivity, matrix compatibility and insertability and offer wide formulation flexibility.
As Basionics are transparent, manufacturers can produce naturally colored as well as tinted products. The wide window of thermal stability allows their use in nearly all common PUR manufacturing and application processes. Basionics are also available as TPU masterbatches.
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Solvents
BASF is a leading producer of dimethyl-formamide (DMF), N,N-dimethylacet-amide (DMAC), N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP) and propylene carbonate (PC) with integrated production sites in Ludwigshafen, Germany and Nanjing, China. Expertise in the production of DMF, DMAC, NMP, NEP and PC combined with fully backward-integrated production sites in all major consumption areas make BASF the poly urethane industry’s supplier and partner of choice.
As the world’s leading chemical company, BASF has many years of experience in DMF, DMAC, NMP, NEP and PC with regard to issues such as health, sustai-nability, product stewardship, safety and the environment. We share this expertise to make our customers more successful.
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The mechanical properties of components made of glassfi ber-reinforced epoxy resins are determined by means of state-of-the-art testing equipment.
Dimethylformamide (DMF)
is a colorless, high-boiling, polar liquid with high solvency power. It is freely miscible with water and easily recycled. DMF is a major solvent in the production of PUR elastomers, spandex fibers and synthetic leather.
Other uses:
Solvent in PAC fiber production
Reaction medium in the production of active ingredients for pharmaceuticals and agrochemicals
Intermediate in numerous industrial processes
Selective absorbent for gases
N-Methyl-2-pyrrolidone (NMP) and N-ethyl-2-pyrrolidone (NEP) are semi-volatile, aprotic, highly polar solvents. Both products are colorless, highly mobile liquids with a faint amine-like odor. NMP and NEP are infinitely miscible with water and most organic solvents.
Applications for NMP and NEP include:
PUR dispersion production
Cleaning of molds and production systems (nozzles, tanks)
Removal of PUR-based paints and resins
Process aid in the manufacture of PUR-based adhesives
N,N-Dimethylacetamide (DMAC) is a colorless, water-miscible and polar liquid which is commonly used as a solvent for industrial applications and organic reactions. DMAC is the solvent of choice for the production of spandex fibers.
Other fields of application for N,N-dimethylacetamide are:
Solvent for the production of PAC fibers
Production of pharmaceuticals and agrochemicals
Solvent and reaction medium for a variety of industrial processes
Propylene carbonate (PC) has a number of beneficial properties and characteristics in urethane chemistry applications. It can be used as a viscosity reducer, compatibilizer, reactive diluent and plasticizer in urethane systems.
Other fields of applications for propylene carbonate are:
Solvent replacement for toxic solvents (low toxicity and non-irritability)
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BASF name International name CAS-no. Mol. weight[g/mol]
TSCA REACH ENCS/IS
Lupragen® N 100 N,N-Dimethylcyclohexylamine 98-94-2 127.2 + registered +
Lupragen® N 101 N,N-Dimethylethanolamine 108-01-0 89.1 + registered +
Lupragen® N 105 N-Methylmorpholine 109-02-4 101.2 + preregistered +
Lupragen® N 106 2,2’-Dimorpholinodiethylether 6425-39-4 244.3 + preregistered MON2, JP
Lupragen® N 107 Dimethylaminoethoxyethanol 1704-62-7 133.2 + preregistered +
Lupragen® N 201 Triethylenediamine 33% sol. in dipropyleneglycol 280-57-9 112.2 + preregistered +
Lupragen® N 203 Triethylenediamine 33% sol. in monoethyleneglycol 280-57-9 112.2 + preregistered +
Lupragen® N 205 Bis(2-dimethylaminoethyl)ether 3033-62-3 160.3 + preregistered +
Lupragen® N 301 Pentamethyldiethylenetriamine 3030-47-5 173.3 + preregistered +
Lupragen® N 400 N,N,N’-Trimethylaminoethylethanolamine 2212-32-0 146.2 + preregistered +
Lupragen® N 500 N,N,N’,N’-Tetramethyl-1,6-hexanediamine 111-18-2 172.3 + preregistered +
Lupragen® N 600 S-Triazine 15875-13-5 342.6 + registered +
Lupragen® N 700 1,8-Diazabicyclo-5,4,0-undecene-7 6674-22-2 152.2 + preregistered +
Lupragen® API N-(3-Aminopropyl)imidazole 5036-48-6 125.2 + preregistered +
Lupragen® DMI 1,2-Dimethylimidazole 1739-84-0 96.1 + preregistered +
Lupragen® NMI 1-Methylimidazole 616-47-7 82.1 + preregistered +
3-Dimethylaminopropane-1-ol 3-Dimethylaminopropane-1-ol 3179-63-3 103.2 + preregistered +
PolyTHF® 650S Polytetramethyleneetherglycol 650S 25190-06-1 650 + exempt +
PolyTHF® 1000 Polytetramethyleneetherglycol 1000 25190-06-2 1000 + exempt +
PolyTHF® 1000S Polytetramethyleneetherglycol 1000S 25190-06-3 1000 + exempt +
PolyTHF® 2000 Polytetramethyleneetherglycol 2000 25190-06-4 2000 + exempt +
1,4-Butanediol 1,4-Butanediol 110-63-4 90.1 + registered MON2, JP
1,6-Hexanediol 1,6-Hexanediol 629-11-8 118.2 + registered +
Comprehensive portfolio of PUR intermediates
Exclusively marketed by Evonik Industries AG
If not specifi ed, b.p. and m.p. measured at 1013 hPa.
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Meltingpoint[°C]
Boiling point[°C]
Purity/content [%]
Low emis-sion
Application
fl exible foam semi-rigid rigid elastomer adhesives TPU slabstock molded foam foam shoe sole coatings
–77 162.3 min. 99.0 (GC)
–59 134.1 min. 99.8 (GC)
–65 115 min. 99.0 (GC)
–28 309 min. 98.0 (GC)
< –70 204 min. 99.0 (GC) +
–39 n.d. 33.1 – 33.5 (titration)
–67 196 33.1 – 33.5 (titration)
< –80 188 min. 97.0 (GC)
< –20 199 min. 98.0 (GC)
< –70 210 min. 98.5 (GC) +
–46 212 – 216 min. 99.0 (GC)
–59 225 not available
–70 262 min. 98.0 (GC)
–68 296 97.0 (GC) +
20 – 40 205 min. 96.0 (GC)
–2 198 min. 99.0 (GC)
–35 159 min. 99.0 +
25 > 250 min. 99.0
26 > 250 min. 99.0
26 > 250 min. 99.0
36 > 250 min. 99.0
20 230 min. 99.5 (GC)
40 – 42 253 – 260 min. 96.0 (GC)
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Capromer™ and Basionics™ are registered trademarks of BASF SE.
PolyTHF® and Lupragen® are registered trademarks of BASF SE in many countries.
BASF name International name CAS-no. Mol. weight[g/mol]
TSCA REACH ENCS/IS
1,5-Pentanediol 1,5-Pentanediol 111-29-5 104.2 + registered +
TMP (Trimethylolpropane) Trimethylolpropane 77-99-6 134.2 + registered +
NEP (N-Ethyl-2-pyrrolidone) 1-Ethyl-2-pyrrolidone 2687-91-4 113.2 + registered +
NMP (N-Methyl-2-pyrrolidone) 1-Methyl-2-pyrrolidone 872-50-4 99.1 + registered +
PC (Propylene carbonate) Propylene carbonate 108-32-7 102.1 + registered +
DMAPA 3-(Dimethylamino)propylamine 109-55-7 102.2 + registered +
N-(2-Aminoethyl)ethanolamine N-(2-Aminoethyl)ethanolamine 111-41-1 104.15 + registered +
Methyldiethanolamine Methyldiethanolamine 105-59-9 119.2 + registered +
Monoethanolamine pure Monoethanolamine pure 141-43-5 61.1 + registered +
Triethanolamine S Triethanolamine S 102-71-6 149.0 + registered +
Triethanolamine pure Triethanolamine pure 102-71-6 149.2 + registered +
Diethanolamine pure Diethanolamine pure 111-42-2 105.1 + registered +
Diisopropanolamine Diisopropanolamine 110-97-4 133.2 + registered +
Isopropanolamine Isopropanolamine 78-96-6 75.1 + registered +
Triisopropanolamine Triisopropanolamine 122-20-3 191.3 + registered +
N4-Amine N,N’-Bis-(3-aminopropyl)-ethylenediamine 10563-26-5 174.3 + preregistered -
Capromer™ PD1-10 Capromer™ PD1-10 69089-45-8 1000 + exempt +
Capromer™ PD1-10A Capromer™ PD1-10A 69089-45-8 1000 + exempt +
Capromer™ PD1-20 Capromer™ PD1-20 69089-45-8 2000 + exempt +
Capromer™ PD1-20A Capromer™ PD1-20A 69089-45-8 2000 + exempt +
Capromer™ PD4-05 Capromer™ PD4-05 36890-68-3 550 + exempt +
Capromer™ PT1-05 Capromer™ PT1-05 37625-56-2 540 + exempt +
If not specifi ed, b.p. and m.p. measured at 1013 hPa.
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Meltingpoint[°C]
Boiling point[°C]
Purity/content [%]
Low emis-sion
Application
fl exible foam semi-rigid rigid elastomer adhesives TPU slabstock molded foam foam shoe sole coatings
–16 240 – 244 min. 97.0 (GC)
58 292 – 297 min. 99.0 (GC)
< –75 213 99.4 (GC)
–24 204.3 min. 99.8 (GC)
–49 240 – 243 min. 99.7 (GC)
< –50 134 min. 99.8 (GC)
< –18 243 min. 99.5
–21 243 min. 99.0
11 170 min. 99.7
8 175 – 185 (2 hPa) 82.0 – 88.0
18-23 336 min. 99.3
27 270 min. 99.3
44.5 – 45.5 249 – 255 min. 99.0
2 158 – 159 min. 99.0
45 301 min. 99.0
–1.5 > 169 min. 93.0
30 – 45 > 250 min. 99.0
30 – 45 > 250 min. 99.0
40 – 50 > 250 min. 99.0
40 – 50 > 250 min. 99.0
15 – 25 > 250 min. 99.0
0 – 15 > 250 min. 99.0
CZ
120
1-01
/12-
1.00
0
Intermediates for the PUR industry
Your benefi ts:
Globally unique portfolio of chemical intermediates
High level of supply reliability
Local presence
Extensive customer service
Wide-ranging support
The data contained in this publication is based on our current knowledge and experience. In view of the many factors that may affect processing and application of our product, the data does not relieve processors from carrying out their own investigations and tests; neither does the data imply any guarantee of certain properties, nor the suitability of the product for a specifi c purpose. Any descriptions, drawings, photographs, data, proportions, weights etc. given herein may change without prior information and do not constitute the agreed contractual quality of the product. It is the responsibility of the recipient of our products to ensure that any proprietary rights and existing laws and legislation are observed. The safety data given in this publication is for information purposes only and does not constitute a legally binding Material Safety Data Sheet (MSDS). The relevant MSDS can be obtained upon request from your supplier or you may contact BASF directly at [email protected]. 2012 edition
bi11_1_7_PUR_12_RZ_12032012.indd 1bi11_1_7_PUR_12_RZ_12032012.indd 1 12.03.2012 9:47:15 Uhr12.03.2012 9:47:15 Uhr