Octadecanoic acid, compd. with 2-(2-aminoethoxy)ethanol (1:1) (cas ) MSDS

Transcription

1 Click for suppliers of this product Octadecanoic acid, compd. with 2-(2-aminoethoxy)ethanol (1:1) (cas ) MSDS Performance Products Metalworking Chemicals Product Information Huntsman Metalworking Chemicals Table of Contents Huntsman Capabilities Huntsman Products Comparison of Important Properties DIGLYCOLAMINE? Agent Bis-(hydroxyethyl) methyl amine (BHEMA) SURFONAMINE? MW-781 Amine XTA-771 Ethanolamines Other Amines Surfactants for the Metalworking Industry Alkylphenol Ethoxylates Alcohol Alkoxylates EO/PO Block Copolymers Alcohol Ethoxylates Fatty Acid and Castor Oil Ethoxylates Phosphate Esters Formulated Emulsifiers Other Products for the Metalworking Industry...45 Alkylate H-230L JEFFOX? WL-series Functional Fluids Glycols Regional Product Offerings Contact Information DEHSCOFIX?, DGA?, DIGLYCOLAMINE?, EMPICOL?, EMPILAN?, EMPIPHOS?, JEFFAMINE?, JEFFOX?, LAUREX?, POGOL?, SURFOL?, SURFONAMINE?, and SURFONIC? are registered trademarks of Huntsman Corporation or an affiliate thereof in one or more, but not all, countries. DMDGA?? is a trademark of Huntsman Corporation of an affiliate thereof in one or more, but not all, countries. CORFREE? is a trademark of Invista North America. TEFLON? is a trademark of E. I. DuPont de Nemours & Company. VITON? is a trademark of DuPont Dow Elastomers LLC.

2 1 SECTION 1 Introduction Huntsman Capabilities our products worldwide, assisted by an extensive distributor network. Huntsman is committed to producing a broad range of the highest quality amines, surfactants and related Huntsman is an innovative supplier. With the support chemicals for the metalworking industry, and is the of state of the art research, development and pilot logical choice to be your key supplier for the formulation facilities we will work closely with you to help of your metalworking fluids. formulate products that meet your exacting needs. Huntsman is an integrated supplier, producing not only Huntsman Products the finished amines and surfactants but many of the Huntsman manufactures a broad range of amines, basic raw materials used to manufacture those products. surfactants, and related products essential in formulating metalworking fluids. Table 1.1 lists Huntsman is a global supplier, manufacturing primary application areas for each of the product products for the metalworking industry in the United types. Similar tables including trademarked product States, Australia, and multiple European countries. names by region can be found in Section 5. Our skilled and knowledgeable sales force markets 2 Introduction Table Huntsman Products for the Metalworking Industry Hard Water Tolerance Aids Metal Cleaning Aids Corrosion Inhibitors Anti-mist Additives Lubricity Additives Alkalinity Control Coupling Agents Anti-Foamants

3 Intermediates Emulsifiers Product Primary Amines Tertiary Amines Polyetheramines Linear Alcohols Alcohol Ethoxylates Alcohol Alkoxylates Alkylphenol Ethoxylates Fatty Acid Ethoxylates Castor Oil Ethoxylates EO/PO Block and Reverse Block Copolymers Phosphate Esters Sodium Isethionate Functional Fluids Glycols Glycol Ethers 3 SECTION 2 Huntsman is a major integrated supplier of amines, metalworking. A comparison of cobalt leaching by many of which have application in the metalworking commonly used metalworking amines is plotted in industry. We have developed and continue to support Figure 2.2. our amine process technologies in fully equipped laboratories and pilot facilities in the United States The ph measurements on solutions of various amines at and Europe. This section demonstrates our ongoing several different concentrations in water are given in Table commitment to our amine customers in the 2.4. These data are indicative of the relative efficiency of metalworking industry. the amines as alkalinity control agents. Generally, DIGLYCOLAMINE? Agent is less alkaline than MEA and Included in Section 2 is information on various MIPA. It is somewhat more alkaline than either DEA or amines commonly used in the metalworking industry. DIPA (diispropanolamine). The first part of this section contains comparison data for these amines while the last part of this Titration curves are presented for several of the more section individually discusses several Huntsman common metalworking amines with some of the more amines used in the metalworking industry. These common metalworking acids in Figures 2.3, 2.4 and 2.5. products include DIGLYCOLAMINE? Agent, bis- (hydroxyethyl) methyl amine (BHEMA), SURFON- Boric acid is a well-known component of metalworking

4 AMINE? MW-781 amine, triethanolamine (TEA), fluids, which imparts both corrosion resistance and diethanolamine (DEA), and others. enhanced biostability. Both salts and condensates of boric acid with a variety of amines have been employed. Comparison of Important Properties Data in the literature suggest that the boric acid adduct of DIGLYCOLAMINE? Agent is quite effective in maintaining A list of amines commonly used in metalworking is ph and resisting biodegradation (Table 2.5). given in Table 2.1, with Huntsman product offerings highlighted. Table 2.2 further discusses commonly Published information (Table 2.6) comparing the tendency used amines in metalworking, listing the CAS to form N-nitrosoamines in prototype synthetic and seminumbers, as well as regulatory information. synthetic cutting fluids shows a pronounced tendency to form these carcinogenic materials from secondary amines Volatility is an important consideration in metalworking like DEA and diisopropanolamine (DIPA). Primary amines, applications where misting is a concern. Data like DIGLYCOLAMINE? Agent, do not show this tendency. included in Table 2.3 and Figure 2.1 illustrate the low volatility of Huntsman products, such as Another important aspect in metalworking is corrosion. DIGLYCOLAMINE? Agent, monoethanolamine (MEA), Aluminum staining/corrosion data is compared in Tables DEA, TEA and BHEMA, relative to other amines 2.7, 2.8, and 2.9. Figure 2.6 compares magnesium commonly used in metalworking applications. staining by various amines. Cobalt leaching is another important factor in 4 Table Amines for Metalworking Physical Properties DGA? Agent MEA AMP MIPA DEA DIPA TEA BHEMA APM Amine Type Primary Primary Primary Primary Secondary* Secondary* Tertiary Tertiary Prim/Tert Appearance Clear and free of suspended material Color, Pt-Co <15 <15 <15 <15 <15 <15 <15 <15 <15 Equivalent Weight ** pka, 20??C ph, 5% aqueous solution Boiling Point,??C, 760 mmhg Vapor Pressure, 20??C, mmhg <0.01 <0.01 <0.01 <0.01 <1 Freezing Point,??C (dry) <-45 Flash Point,??C Viscosity, cst, 30??C Environmental, Health & Safety Concerns Dermal LD50, mg/kg > > >3000 >3000 Oral LD50, mg/kg >2000 Acute Fish LC50, mg/l 460 > >450 Acute Daphnia EC50, mg/l 190 > Acute Algae IC50, mg/l ?? > Mutagenic No No No No (*) (*) No No

5 Dermal Sensitizer No No No No No No No No WGK Classification 1 1?? Data sources: Huntsman, literature * Secondary amines prone to N-nitrosamine formation Huntsman products in bold type. **Equivalent weight is for primary amine function only 5 SECTION 2 Table Common Amine Components of Metalworking Fluid Formulations European U.S. DOT Packing Exposure CAS# Classification Classification Group Limits Authority DIGLYCOLAMINE? Agent 2-(2-aminoethoxy)ethanol Corrosive Corrosive III None?? MIPA Isopropanolamine Corrosive Corrosive II None?? AMP amino methyl propanol alternative Irritant None?? None?? BHEMA Bis-(hydroxyethyl)methylamine Irritant None?? None?? TEA Triethanolamine None None?? 5 mg/m3 TWA ACGIH TLV DEA Diethanolamine Irritant None?? 15 mg/m3 TWA ACGIH TLV MEA Monoethanolamine Harmful Corrosive III 6 mg/m3 TWA OSHA PEL 6 Table Relative Volatility of Selected Amines Used in Metalworking Vapor Pressure, mmhg Boiling Point,??C, Flash Point, 20??C 100??C 150??C 760 mmhg??c DIGLYCOLAMINE? Agent MEA MIPA AMP ??

6 Figure Volatility of Some Common Metalworking Amine Solutions* Amine in Vapor Phase (Wt%) *Plots correspond to a 10 wt% aqueous amine sample and were constructed using data obtained in vapor-liquid equilibrium determinations. 7 SECTION 2 Figure Cobalt Leaching by Commonly Used Metalworking Amines* *Samples are 1 wt% aqueous solutions of amine containing 1500 ppm cobalt powder. The ph of each solution is adjusted to the desired ph level with acetic acid. Dissolved cobalt is measured after 21 days. 8 Table ph of Metalworking Amines as a Function of Concentration at 25??C1 Amine Concentrate (wt%) DIGLYCOLAMINE? Agent 2-(2-aminoethoxy)ethanol MEA Monoethanolamine JEFFAMINE? D-400 Polyetheramine AMP amino methyl propanol alternative MIPA Monoisopropanolamine DEA Diethanolamine DIPA Diisopropanolamine TEA Triethanolamine BHEMA Bis-(hydroxyethyl)methylamine

7 DMDGATM Aminoalcohol N,N-dimethyl-2-(2-aminoethoxy)-ethanol APM Aminopropylmorpholine ph data was determined using a pre-calibrated Beckman 12pH Meter and Cole Parmer sealed combination electrode with a silver/silver chloride reference 1 electrode. Solutions were allowed to equilibrate 10 minutes prior to measurement. 9 SECTION 2 Figure Titration Curves of Various Metalworking Amines with Decanoic Acid Figure Titration Curves of Metalworking Amines with Isononaoic Acid 10 Figure Titration Curves of Metalworking Amines with CORFREE? M1 Corrosion Inhibitor ml of 5% amine solution Table ph Stability of Boric Acid Derivative of Aminoalcohols1 ph Initial 6 days 12 days 18 days 30 days % Change Adduct with DIGLYCOLAMINE? Agent Odor none none none none none Adduct with MEA Odor none none none weak weak Adduct with DEA Odor none none none none none Adduct with TEA Odor none none none none none??antimicrobial Properties of the Products from the Reaction of Various Aminoalcohols and Boric Anhydride?? 1

8 S. Wantanabe, T. Fujita, M. Sakamoto, and W. Aono Materials Chemistry and Physics, Volume 19 (1988), pp SECTION 2 Table Nitrosoamine Formation in Synthetic and Semi-Synthetic Cutting Fluids Semi-synthetic Cutting Fluid1 ppb Nitrosoamine Secondary Amine DEA 336 Diisopropanol Amine 414 Primary Amine MEA 14 Monoisopropanol Amine 18 DIGLYCOLAMINE? Agent 24 Tertiary Amine TEA 113 Control 9 Synthetic Cutting Fluid2 ppb Nitrosoamine Secondary Amine DEA 609,000 Primary Amine MEA None detected DIGLYCOLAMINE? Agent None detected Conditions: 5% emulsion, 50 ppm Na nitrite, 60??C, 1 week 1 Reference: J. H??bner in T + S Tribologie und Schmierungstechnik, 3, 1996 Literature: R.N. Loeppky, T.J. Hansen, and L.K. Keefter, Food and Chemical Toxicology, Vol. 21, , Nitrite-free cutting fluid after exposure to nitric oxide in air for three hours Table Aluminum Staining/Corrosion Summary of Results?? Aluminum staining/corrosion is ph dependent?? Aluminum staining/corrosion is also dependent on the presence of other common additives (such as fatty acids)?? Tests run at ph=8.8 suggest that DGA? Agent may provide an advantage over other amines?? Solutions of TEA showed much more significant staining/corrosion than any other amines tested?? Test time was 24 hours at ambient temperature?? Corrosion documented by weighing the test coupons before and after the test; dissolved Al in solution measured by ICP 12 Table Aluminum Staining/Corrosion

9 Dissolved Al (ppm) Amine* Al 7075 Al 6061 Al 2024 Al 390 DGA? Agent AMP TEA XTA BHEMA DEA MEA?????? 10 Blank <1 <1 <1 <1 * 2.5 weight % aqueous solution of amine; ph adjusted with acetic acid 13 SECTION 2 Table Aluminum Staining/Corrosion with Fatty Acid Amine Dissolved Al (ppm) Isononanoic acid salt* Al 7075 Al 6061 Al 2024 Al 390 DGA? Agent AMP TEA XTA BHEMA <1 <1 DEA 2.5 <1 1.2 <1 MEA 1.9 <1 2.6 <1 Blank 4.1 < * 2.5 weight % aqueous solution of salt (1:1); ph adjusted with KOH Figure Effect of Amines on Magnesium % Wt Loss From Coupons 14 DIGLYCOLAMINE? Agent DIGLYCOLAMINE? Agent is an essentially colorless, Table 2.13 lists the countries with DIGLYCOLAMINE?

10 slightly viscous liquid. The product is a non-volatile Agent registrations. Table 2.14 lists TSCA registrations primary amine with a low tendency to leach cobalt, for amides and salts of DGA? Agent. aluminum, or copper. Features and benefits of DGA? Agent are listed in Table A comparison of hard water tolerance of salts of neodecanoic acid with either DGA? agent or DEA is DIGLYCOLAMINE? Agent has an excellent toxicity presented in Table profile as summarized in Table Numerous physical properties of DGA? Agent are listed in Table Table Features and Benefits of DIGLYCOLAMINE? Agent in Metalworking Features Benefits?? Primary Amine?? DEA free?? Isomeric with DEA?? Reacts readily with acids to form amides and salts?? Inventory listed (TSCA, EINECS, MITI, DSL, AICS)?? Stoichiometrically equivalent to DEA?? Used commercially in U.S. and Europe as DEA replacement?? Readily available globally?? Huntsman manufactures in U.S. and Europe?? Minimal disposal problems?? Low toxicity profile?? Reduced volatility and respiratory concerns; Good cold weather handling?? Non-mutagenic?? Similar to DEA in providing buffering capacity?? Non-dermal sensitizer?? Amides provide lubricity, emulsification, hard water stability?? Lower volatility, higher boiling and flash points than other DEA substitutes?? Lower freezing points than other DEA substitutes?? Provides buffering and corrosion protection?? Lime-tolerant?? Readily forms amides 15 SECTION 2 Table DIGLYCOLAMINE? Agent Toxicity Profile Mammalian Toxicity Oral LD g/kg in rats; considered slightly toxic by ingestion (1991). Dermal LD50 Greater than 3.0 g/kg in rabbits; considered practically non-toxic by dermal absorption (1990). Dermal Irritation Draize dermal irritation score in rabbits is 8.0 of 8.0; considered to be a dermal corrosive (1992). Ocular Irritation Due to dermal corrosivity, an ocular irritation study is considered to be inappropriate and has not been performed. Draize ocular irritation score (rabbit) is estimated to be 50 to 80/100; considered to be severely irritating/corrosive to the eyes. Dermal Sensitization Not a sensitizer in guinea pigs when induced and challenged at 105 using the Beuhler study protocol (1991). Genetic Toxicity Ames Assay Negative with and without metabolic activation in a plate incorporation assay, using concentrations up to 10,000 ug/plate in Salmonella tester strains TA 98, TA 100, TA 1535, TA 1537, and TA 1538 (1982). UDS Assay Negative at culture concentrations up to 1% in DMSO. This concentration was the maximum non-cytotoxic dosage under the test protocol (1982). Cell Transformation Test Negative at culture concentration up to 1563 nl/ml. This concentration was the maximum non-cytotoxic dosage under the test protocol (1982).

11 16 Table Physical Properties of DIGYCOLAMINE? Agent Boiling point,??c, 760 mmhg 221 Critical constants* Critical temperature,??c Critical pressure, psi Critical density, g/cc Density, g/ml 60??F ??F Flash point,??f, PMCC 255 Freezing point,??c Heat of vaporization, 760 mmhg, Btu/lb Ionization constant, 25??C, KD 3.6 x 10-5 Refractive index, nd, 20??C Specific gravity, 20/20??C Specific heat of liquid, Btu/lb/??F 60??F ??F Thermal conductivity, 68??F, Btu/hr, sq ft,??f/ft Vapor pressure, 68??F, mmhg 0.004* Viscosity, 60??F, cp 40 Weight, 60??F, lb/gal 8.8 * calculated Table DIGLYCOLAMINE? Agent Registrations Country Inventory CAS# United States TSCA Europe EINECS Canada DSL Australia AICS Japan MITI (2)-3202 Korea ECL SECTION 2 Table DIGLYCOLAMINE? Amide and Salt Registrations Inventory PMN# Amides CAS#

12 TSCA DGA? Amide of Neodecanoic acid TSCA DGA? Amide of Coco Fatty acid TSCA DGA? Amide of Dodecanoic acid TSCA DGA? Amide of Decanoic acid TSCA DGA? Amide of Castor-oil Fatty acid Testing Required DGA? Amide of Tall Oil Fatty acid Testing Required DGA? Amide of Octadecanoic acid Testing Required DGA? Amide of Isooctadecanoic acid Testing Required DGA? Amide of Soya Fatty acid Salts TSCA DGA? Salt of Tall Oil Fatty acid TSCA DGA? Salt of Octadecanoic acid TSCA DGA? Salt of Isooctadecanoic acid TSCA DGA? Salt of Soya Fatty acid TSCA DGA? Salt of Castor-oil Fatty acid TSCA DGA? Salt of Coco Fatty acid TSCA DGA? Salt of Dodecanoic acid TSCA DGA? Salt of Neodecanoic acid TSCA DGA? Salt of Decanoic acid TSCA DGA? Salt of Nonanoic acid TSCA DGA? Salt of Boric acid TSCA DGA? Salt of Dodecanedioic acid TSCA DGA? Salt of Undecanedioic acid TSCA DGA? Salt of Decanedioic acid TSCA DGA? Salt of CORFREE? M1 inhibitor TSCA DGA? Salt of 3,5,5-Trimethyl-hexanoic acid Table Hard Water Tolerance of Neodecanoic Acid Salts of DIGLYCOLAMINE? Agent vs. DEA Hardness, ppm Temperature, 25??C DIGLYCOLAMINE? Agent C C C C

13 DEA C C SH SH Temperature, 60??C DIGLYCOLAMINE? Agent C C C C DEA C SH SH SH Notes: Salts used at 1% level Acid type influences hard water tolerance C = Clear SH = Slight Haze 19 SECTION 2 DIGLYCOLAMINE? Agent Data comparing the physical properties of DGA? vapor pressure of DGA? Agent indicate DGA? Agent Agent and another commonly used metalworking is a less volatile amine. This could be an important amine are given in Table Both products are factor where misting and odor are concerns. Both relatively strong amines with about the same amines have similar toxicity profiles. equivalent weight. The boiling point, flash point, and Table DGA? Agent Physical Properties Physical Properties DGA? Agent AMP Amine type Primary Primary Equivalent weight Boiling point,??c, 760 mmhg Vapor Pressure, 20??C, mmhg Freezing Point,??C Viscosity, cst, 10??C ??C ph, 5% aqueous solution Flash point,??c Environmental, Health, and Safety Dermal LD50, mg/kg >3000 >2000 Oral LD50, mg/kg Acute fish LC50, mg/l Acute daphnia EC50, mg/l Acute algae IC50, mg/l Mutagenic No No Dermal Sensitizer No No

14 20 Because AMP is a slightly stronger amine than DGA? available for buffering. Inclusion of TEA will increase Agent, it gives a directionally higher ph in solution the amount of amine present without appreciably (Table 2.17). When these amines are used to provide increasing the ph. The effect of blending TEA with reserve alkalinity (buffering), we recommend the either DGA? Agent or AMP on ph and alkalinity of 5% inclusion of a weaker amine like TEA (Triethanolamine). aqueous solutions is given in Table The data Reserve alkalinity is a function of the amount of amine indicate AMP is a more basic amine giving a present. With strong amines, less amine is required to directionally lower reserve alkalinity with TEA than reach a given ph target, hence reducing the amount DGA? Agent with TEA. Table ph and Reserve Alkalinity of 5% Aqueous Amine Solutions ph Reserve Alkalinity 1 TEA 10.4?? DGA? Agent AMP DGA? Agent/TEA (2.5%/2.5%) AMP/TEA (2.5%/2.5%) As neodecanoic acid salt (ASTM D1121) 1 The breakpoints obtained from iron chip corrosion tests DGA? Agent, weight % AMP, and 9.27 weight % on borate salts of DGA? Agent and AMP are provided boric acid. The ph of all solutions was The tests in Table DGA? Agent and AMP are seen to be were run according to ASTM D , utilizing 10 equivalent in their effect on corrosion of cast iron chips dilutions of the test solutions in calcium chloride water. A as defined by the ASTM D4627 test. second set of tests were also performed by making the dilutions using calcium chloride water containing 10 times The test solutions were made up of 1:1 amine/boric acid, at the standard method concentration. There was no 1.5M concentration. This corresponds to weight % observable effect on the breakpoints. Table Amine Borate Chip Rust Test Results Amine Breakpoint Breakpoint (10X) DGA? Agent/Borate DGA? Agent/Borate - repeat AMP/Borate AMP/Borate - repeat SECTION 2

15 DGA? Agent and AMP have a similar cobalt leaching solutions of the neodecanoic acid salts of both amines, profile, while DGA? Agent is better toward copper are essentially equivalent. (Table 2.19). Foam properties, as measured on 1% Table 2.19* - Cobalt and Copper Leaching Comparison Co Cu DI water (control) DGA? Agent AMP *Angus Chemical Company data Electrochemical tests1 were performed to measure the Corrosion of carbon steel was very low, at an average corrosion rate of aluminum and carbon steel in amine- of 0.05 mpy. The data are given in the table below. We borate solutions. The corrosion rate of aluminum in the conclude on the basis of this testing there are no presence of only the amine borates or amine borates difference in the corrosion protection for aluminum and and KOH, used to adjust to a constant ph, was steel provided by the amine borates prepared from moderate, in the range of 2.4 to 6.0 mpy. There was DGA? Agent, DEA, and AMP. essentially no difference among the three amines. Table Aluminum Corrosion Rates Amine Salt ph Aluminum (mpy) Steel (mpy) DGA? Agent Borate ?? ?? DEA Borate ?? ?? AMP Borate ?? ?? DGA? Agent Borate ?? 0.9 Not determined DEA Borate ?? 1.9 Not determined AMP Borate ?? 1.2 Not determined The amines were prepared as 1:1 mole ratio salts with boric acid at a concentration of 0.1M. The solutions were tested at the as-prepared ph (shown in Table 2.20) 1 and also at a ph value of 10.1, adjusted using KOH. The corrosion rates were measured using electrochemical polarization resistance over a four-hour period. Aluminum alloy 7075 (UNS A97075) and 1020 carbon steel were freshly polished before each test. All tests were performed at room temperature (22??C) under continuous aeration and with moderate stirring. 22 Handling, Storage and Shipping of DIGLYCOLAMINE? Agent General area to heat the tank contents using low-pressure steam should be built into the tank about six inches above the floor. The coils should be constructed in such a manner

16 The handling and storage of DIGLYCOLAMINE? Agent as to allow the condensate to drain. Stainless steel coils present no unusual problems. Huntsman Corporation??s are preferred, particularly when low color Technical Services team is available to assist those DIGLYCOLAMINE? Agent is important. If steam heat is persons desiring additional information. to be used continuously to prevent high viscosities or Maintaining Specifications freezing, a temperature regulator that throttles either the steam or condensate should be installed. DIGLYCOLAMINE? Agent is hygroscopic and will In situations where the ambient temperature is low, tank absorb water vapor when exposed to a moist insulation is desirable. Asphalt-cork or urethane foam atmosphere. If water content is to be minimized, a dry insulation sprayed onto the outer wall is satisfactory. If inert gas pad under a few ounces of pressure should be a nitrogen pad is used, pressure relief and vacuum relief used on the storage tanks. A gas pad should also be valves of a suitable capacity should be installed. The used if low color is important, since absorbed system may consist of a cylinder of nitrogen, a pressure atmospheric oxygen and carbon dioxide will cause reducing valve, a pressure relief valve, and a line to the DIGLYCOLAMINE? Agent to develop color. Since top of the storage tank. Tankage should be diked and DIGLYCOLAMINE? Agent is basic, it will react with electrically bonded and grouped. acidic gases; hence carbon dioxide and natural gas containing acidic sulfur compounds cannot be used. Transfer Lines Nitrogen is quite suitable. Carbon steel transfer lines at least two inches in diameter The solvent properties and alkaline nature of and joined by welds or flanges are suitable. Screwed DIGLYCOLAMINE? Agent should also be considered joints are subject to failure unless back-welded because when installing handling and storage facilities. DIGLYCOLAMINE? Agent will leach conventional pipe DIGLYCOLAMINE? Agent may react with copper to dopes. U.S. Rubber 899 gasket material, polypropylene, form complex salts. The use of copper and alloys Teflon? elastomer, or their equivalents are satisfactory for containing copper should be avoided in equipment that use with flanged connections in DIGLYCOLAMINE? will contact DIGLYCOLAMINE? Agent or its aqueous Agent service. Avoid the use of nitrile rubbers such as solutions. Carbon steel storage tanks constructed neoprene, Buna-N or Viton? rubber. according to a recognized code are generally satisfactory. In cases where low color is important, If the ambient temperature is below 20??F, the transfer stainless steel is preferred. line for the pure product should be steam traced and insulated. Steam tracing can be accomplished by DIGLYCOLAMINE? Agent is not compatible with affixing copper tubing of approximately 3/8-inch phenolic resin linings. Steam coils with sufficient surface 23 SECTION 2

17 diameter to the underside of the line, insulating the tube constructed of welded carbon steel and have bottomto the line, and using low-pressure steam in the tubing. unloading fittings and steam coils. For flexible connections, stainless steel hose is preferred to rubber since rubber will generally deteriorate in Deliveries can also be made in insulated, stainless steel, DIGLYCOLAMINE? Agent service and increase the full or compartmented tank wagons with steam coils. If color of the product with time and temperature. requested, tank wagons can be equipped with unloading pumps and hoses. Systems that are insulated and steam traced should be preheated in cool weather before being put into Drums of DIGLYCOLAMINE? Agent can be shipped in service. Normally, 15 to 30 minutes of applying steam truckload or less-than-truckload quantities. The net to the tubing will adequately warm, but not overheat, weight of a drum is 480 pounds; the gross weight is the system. approximately 519 pounds per drum. Drums are UN1A1 or UN1H1, nonreturnable. Transfer piping and pumps may be equipped with a nitrogen padding system so the DIGLYCOLAMINE? Under U.S. Department of Transportation (DOT) and Agent can be pressured out of the lines when an Canadian Transportation of Dangerous Goods (TDG) extended idle period is contemplated. This practice regulations, the proper shipping name for will help losses and color increases that would result if DIGLYCOLAMINE? Agent is??2-(2-aminoethoxy)ethanol??, the DIGLYCOLAMINE? Agent were allowed to remain identification number UN This product is considered in the lines. a corrosive material (TDG hazard class 8) and requires a??corrosive?? label for shipping. Shipping Information For further information, please refer to the Material Delivery ofdiglycolamine? Agent can be made in Safety Data Sheet (MSDS). 10,000 and 20,000-gallon tank cars. These cars are 24 BHEMA BHEMA is a low-volatility tertiary amine which may summarized in Table Toxicity and be useful as an alternative to TEA. It has low acute environmental profiles are presented in Tables 2.22 toxicity, and low nitrosamine potential. These and Registration information for salts of features, as well as other features of BHEMA are BHEMA are listed in Table Table Features and Benefits of BHEMA Features Benefits?? Alternative to TEA?? Low volatility, which reduces airborne exposure?? Low mammalian and aquatic toxicity?? Not classified as corrosive under DOT?? Low potential for nitrosamine formation?? Shows lower tendency to stain than TEA?? Effective in single amine formulations?? Slightly stronger base and lower molecular weight than TEA, so less amine is required for ph development?? Good reserve alkalinity?? Good copper and cobalt leaching characteristics Table BHEMA Toxicity Profile Test Result Interpretation Dermal LD50 - Rabbit >2000 mg/kg Practically nontoxic Dermal Irritation - Rabbit None -> slightly irritating

18 Eye Irritation - Rabbit Irritating BHEMA is alkaline. 90-day subchronic dermal study - rat LOAEL: 250 mg/kg/d Effects limited to skin effects from irritation NOAEL: 100 mg/kg/d Genotoxicity Negative In-vivo and in-vitro studies Data Source: IUCLID monograph 25 SECTION 2 Table BHEMA Environmental Profile Test Value Interpretation Octanol:water partition coefficient (log Kow) Very water soluble; low bioaccumulation potential Fish Toxicity 3 species LC mg/l Practically nontoxic Invertabrate Toxicity (Daphnia) EC mg/l Practically nontoxic Algal Tox EC mg/l EPA slightly toxic Data Source: IUCLID monograph Table BHEMA Salt Registrations TSCA, DSL and EINECS Registrations Pending Inventory PMN# Salts CAS# TSCA P BHEMA Salt of CORFREE? M1 inhibitor TSCA P BHEMA Salt of Tall Oil Fatty Acids TSCA P BHEMA Salt of Neodecanoic Acid TSCA P BHEMA Salt of Nonanoic Acid TSCA P BHEMA Salt of Decanoic Acid Data Source: IUCLID monograph 26 SURFONAMINE? MW-781 Amine SURFONAMINE? MW-781 amine is butoxypropyl benefits are discussed in Table Figure 2.7

19 amine. It is a water white liquid with a low viscosity displays the physical properties for SURFONAMINE? and very low molecular weight. More features and MW-781 amine. Table Features and Benefits of SURFONAMINE? MW-781 Amine Features Benefits?? Strong primary amine (7.6 meq/g total amine)?? Multipurpose additive for synthetic and semi-synthetic formulations?? Possible candidate for Borate production?? Viscosity is 2 cst; Melting point is -47oC?? Very low molecular weight (131 g/mol)?? Has surfactant properties; coupling agent/solubilizer (somewhat foamy?? Inventory listed (TSCA, ENICS, NDSL) if neutralized to a low ph)?? Possible vapor-phase corrosion inhibitor SURFONAMINE? MW-781 Amine Physical Properties Figure SECTION 2 Ethanolamines The ethanolamines used for metalworking are MEA years in metalworking applications. MEA and TEA are (Monoethanolamine), DEA (Diethanolamine), and TEA often used in combination with each other. MEA has a (Triethanolamine). DEA has been used for a number of high ph and TEA has a low ph. Other Amines Some other metalworking amines that can be used polyoxypropylenediamine, JEFFAMINE? D-400 include XTA-771, JEFFAMINE? D-2000 polyoxypropylenediamine, and JEFFAMINE? T-403 polyoxypropylenediamine, JEFFAMINE? D-230 polyetheramine. XTA-771 XTA-771 is a polyoxyalkylene amine with three and benefits are listed in Table primary amine groups per molecule. The features Table Features and Benefits of XTA-771?? Low tendency to leach cobalt from tooling?? Low tendency to leach copper?? Provides added lubricity?? Three primary amine groups per molecule JEFFAMINE? D-2000 Polyoxypropylenediamine JEFFAMINE? D-2000 polyoxypropylenediamine acts as and benefits are listed in Table a defoamer in metalworking applications. The features

20 Table Features and Benefits of JEFFAMINE? D-2000 Amine?? Hydrophobic amine?? Gives defoaming performance in semi-synthetic, but especially synthetic formulations?? Fatty acids amides of JEFFAMINE? D-2000 amine may work even better 28 SECTION 3 Surfactants for the Metalworking Industry Alkylphenol Ethoxylates Nonylphenol Ethoxylates?? SURFONIC? N Series Surfactants The main area of application in metalworking fluids for Nonylphenol ethoxylates are also widely used in metal the SURFONIC N series surfactants is in the cleaning compounds, where they act to scavenge emulsification of oils. Nonylphenol ethoxylates (NPEs) residual fluids, to enhance wetting and rinsing of parts, are highly effective materials for formulating soluble and to disperse swarf left on parts. Formulations based oil, semisynthetic and metal cleaning compounds. on NPEs can be used to clean parts from stamping and These surfactants have excellent emulsification forming operations where they help to disperse waxy properties when used with naphthenic and paraffinic carriers left from the lubricant. oils. In general two or three ethoxylates of different Hydrophile/Lipophile Balance (HLB) are blended in The wetting performance of the SURFONIC N series order to get the best emulsification, especially when products as a function of ethylene oxide (EO) content is formulating products for high hard water tolerance. illustrated in Figures 3.1 and 3.2. The maximum wetting Higher HLB products will improve hard water performance of the water-soluble SURFONIC N series tolerance and hinder soft water tolerance. products is seen with products containing moles of EO per mole of nonylphenol. (Fig. 3.1) Combinations of NPEs such as SURFONIC products Products containing 15 or more moles of EO are useful N-95 with N-40 or N-102 with N-60 are excellent as dispersants for graphite, metal cuttings and the like. starting points for formulation work. The nonylphenol ethoxylates tend to have lower foam and lower pour Many cleaning formulations use caustic additives to points than the equivalent alkyl alcohol ethoxylates. The help saponify fatty materials on the substrate. In SURFONIC N series products are biodegradable and order to make NPEs soluble in potassium hydroxide are compatible with sulfonates, fatty acid salts and (KOH), for instance, a phosphate ester can be used. most other metalworking additives. To complete a Figure 3.2 shows the effectiveness of a phosphate formulation, products such as an amide based on ester at solubilizing SURFONIC N-95 surfactant in DIGLYCOLAMINE? Agent for corrosion control and KOH solutions. lubricity, PEG esters for lubricity, phosphate esters for extreme pressure (EP) enhancement and amines for The physical and surfactant properties of the alkalinity enhancement can be added. SURFONIC N series products are shown in Table SECTION 3 Surfactants for the Metalworking Industry Table SURFONIC? N-Series Nonylphenol Ethoxylates Pour Specific Wetting Ross Miles Solubility? SURFONIC Appearance Point, Gravity, Viscosity, Cloud Time1, CMC, Foam2, 100 SUS 100 SUS Product at 25??C HLB??C 25/25??C cps, 25??C Point seconds ppm mm, Initial Naphthenic Paraffinic Water Function

21 N-31.5 Clear liquid S S I Emulsifier for soluble oils and semisynthetics N-40 Clear liquid S S I Emulsifier for soluble oils and semisynthetics N-60 Clear liquid S I D Emulsifier for soluble oils and semisynthetics N-85 Clear liquid I I S Emulsifier for soluble oils and semisynthetics N-95 Clear liquid I I S Emulsifier for soluble oils & semisynthetics, metal cleaners N-100 Clear liquid I I S Emulsifier for soluble oils & semisynthetics, metal cleaners N-102 Clear liquid I I S Emulsifier for soluble oils & semisynthetics, metal cleaners N-120 Clear liquid I I S Emulsifier for soluble oils & semisynthetics, metal cleaners N-150 White semisolid I I S Improves hard water tolerance of soluble oil and semisynthetics NB-307 Clear liquid I I S Improves hard water tolerance of soluble oil and semisynthetics NB-407 Clear liquid I I S Improves hard water tolerance of soluble oil and semisynthetics 0.1% solution, 25??C 0.1% solution, 120??F Water titration, mls H2O to cloud??c, 1% aqueous solution??c, 1% surfactant in 10% NaCl Surfactants for the Metalworking Industry Figure Draves Wetting Times for Water-Soluble SURFONIC? N Series Products Figure Effect of Phosphate Ester on Solubility of SURFONIC? N-95 surfactant KOH Solutions

22 4% SURFONIC? N-95 surfactant in KOH solutions 31 SECTION 3 Surfactants for the Metalworking Industry Octylphenol Ethoxylates?? SURFONIC? OP Series Surfactants The SURFONIC OP series surfactants are ethoxylates of and semisynthetic formulations. The SURFONIC OP octylphenol. The properties of octylphenol ethoxylates series products are stable in dilute hydrochloric and (OPEs) are similar to those of nonylphenol ethoxylates phosphoric acids. This characteristic suggests usefulness of similar HLB. in acid cleaning, pickling and phosphating formulations. Three main application areas exist in metalworking for The physical and surfactant properties of the SURFONIC OPEs: acid-based cleaners, emulsifiers for soluble oils, OP series products are shown in Table 3.2. Table SURFONIC? OP Series Octylphenol Ethoxylates Pour Specific Wetting Solubility? SURFONIC Appearance Point, Gravity, Viscosity, Cloud Time1, CMC, 100 SUS 100 SUS Product at 25??C HLB??C 25/25??C cps, 25??C Point seconds ppm Naphthenic Paraffinic Water Function OP-15 Liquid S S I Oil soluble coupler and defoamer for semisynthetic and soluble oil formulations OP-35 Liquid S S I Emulsifier for soluble oil formulations OP-70 Liquid S S S Emulsifier for semisynthetic formulations OP-100 Liquid I I S Emulsifier for semisynthetic formulations. Wetting agent for phosphoric and hydrochloric acids OP-120 Liquid I I S Improves hard water tolerance of soluble oil and semisynthetic formulations 0.1% solution, 25??C Water titration, mls H2O to cloud??c, 1% aqueous solution??c, 1% surfactant in 10% NaCl Surfactants for the Metalworking Industry

23 Alcohol Alkoxylates?? SURFONIC? LF, P and JL Series Surfactants The SURFONIC? LF and P product families are made The SURFONIC LF and P series products offer a boost up of ethoxylated, propoxylated linear alcohols. The in lubricity, making them multifunctional in semisynthetic choice of alcohol and the addition patterns for ethylene and synthetic formulations. Falex wear data are offered oxide (EO) and propylene oxide (PO) give the on a simple formulation containing several of these alkoxylated products their unique properties. products. When the formulation is changed to include a phosphate ester (SURFONIC PE-2258 surfactant), The alcohol alkoxylates are ideally suited for dramatically improved Falex wear performance is metalworking operations. They tend to have low foam observed. The synergy between the alkoxylated generation characteristics and some products can act nonionic surfactant and the anionic phosphate ester is as defoamers in water-based systems. All of the also observed with the SURFONIC POA block surfactants in this group will solubilize the components copolymer surfactants. By careful selection of the of carboxylate-based corrosion inhibitors in water. phosphate ester and the SURFONIC LF or P series These surfactants are best suited to synthetic and product, it is possible to get emulsification, semisynthetic formulations. Several products such as solubilization, lubricity, extreme pressure characteristics SURFONIC P1 surfactant are also used in soluble oil and corrosion protection in one pair of surfactants. The formulations. SURFONIC LF-18 surfactant is useful in multifunctional nature of these products makes them low-foam semisynthetic cutting fluids. ideal candidates for many metalworking formulations. SURFONIC P5 surfactant is used in some acid cleaners SURFONIC? JL-80X surfactant is used in some metal and in rinse aid applications. Several of the SURFONIC cleaning operations. The unique structure of this LF series products, particularly SURFONIC LF-37 and product eliminates the gel phase common to alcohol LF-18 surfactants are useful as rinse aid and cleaning ethoxylates in aqueous solutions. This characteristic actives in metal cleaning operations. allows the formulator to blend the surfactant into a formulation without regard to any gelling problems. SURFONIC LF-18 surfactant is used in the production of low-foaming, highly effective microemulsion cleaners The physical and surfactant properties of the using d-limonene as the solvent phase. Formulations of SURFONIC LF and P series products are shown in this type can be used to remove a variety of Table 3.3. metalworking compounds from metal parts. The formulations have very low foam and can be used in A comparison of the dynamic surface tension spray applications. characteristics of the SURFONIC alcohol alkoxylates is presented in Figure SECTION 3 Surfactants for the Metalworking Industry Table SURFONIC? LF, P and JL Series Alcohol Alkoxylates Falex Wear, 875 pounds Pour Specific Cloud Wetting Formulation A Formulation B Ross Miles Solubility? SURFONIC Appearance Point, Gravity, Viscosity, Point,??C Time1, Teeth Wear (T) CMC, Foam Height2, 100 SUS 100 SUS Teeth Wear Product at 25??C HLB??C 25/25??C cps, 25??C 1% aq. seconds Torque in-lbs (IP) ppm mm, Initial/ 5 Min. Naphthenic Paraffinic Water Function LF-17 Clear liquid T 6.6 6/0 I I D Wetting agent for 15 IP acid cleaning operations, low foam emulsifier/rinse aid LF-18 Clear liquid T /0 I I D Low foam additive for 21 IP semisynthetic and synthetic formulations, active defoamer in metal cleaning operations

24 LF-37 Clear to T /0 S I S Low foam emulsifier hazy liquid at 100??F 29 IP for semisynthetic and synthetic formulations LF-41 Clear to T /0 I I S hazy liquid 17 IP P1 Clear to T /0 S S S Solubilizer/emulsifier hazy liquid 19 IP for semisynthetic formulations. Emulsifier/ rinse aid for metal cleaners. Low foam. Wetting agent in dilute acid. P3 Clear to T /11 S I S Rinse aid for cleaners/ hazy liquid 22 IP secondary emulsifier for semisynthetic, wetting agent in dilute acid. P5 Clear to T /5 S I S Hydrophilic emulsifie hazy liquid 20 IP for semisynthetic, soluble in dilute acid P6 Clear to T /0 I I D Low foam additive for hazy liquid 15 IP semisynthetic and synthetic formulations, active defoamer in metal cleaning operations. L4-29X Solid T I I S High molecular at 100??F 15 IP weight emulsifier for semisynthetic and soluble oils, offers some thickening JL-80X Clear liquid T 83 75/70 I I S Prime surfactant in 22 IP cleaners 0.1% solution, 25??C 0.1% solution, 120??F??C, 10% in 25% butyl diglycol Formulation A: 1% TEA, 1% SURFONIC PE-2258 phosphate ester, 1% SURFONIC surfactant, 97% water. Formulation B: 0.17% TEA. 0.15% CORFREE? M-1 inhibitor, 0.07% DGA? Agent, 0.6% SURFONIC surfactant, 99% water. 34 Surfactants for the Metalworking Industry Figure Dynamic Surface Tension of SURFONIC? Alcohol Alkoxylates Surface Tension, mn/m Bubble rate, bubbles/second

25 35 SECTION 3 Surfactants for the Metalworking Industry EO/PO Block Copolymers?? SURFONIC? POA Series Surfactants The SURFONIC? POA block copolymers are very useful Synthetic Formulations in a variety of metalworking operations. These products are made by the sequential addition of ethylene oxide Synthetic formulations depend on products like the and propylene oxide. The functional attributes of these SURFONIC POA block copolymers for low-foam products?? defoaming, wetting, lubricity, solubilization, characteristics, enhanced solubilization of the corrosion emulsification, thickening and dispersion?? all depend inhibitor salts, and a major part of the system lubricity. on the ratio of ethylene oxide to propylene oxide, the The SURFONIC POA products have an inverse solubility molecular weight of the product and the blocking coefficient, which means that at some temperature, pattern of the molecule. Properties of the SURFONIC known as the cloud point, the nonionic surfactant will POA products are given in Table 3.4. come out of solution and act as an oil. When the temperature drops below the cloud point, the surfactant Soluble Oils becomes soluble again and redissolves into the water. The lubricity offered by many nonionic surfactants is Small amounts of low HLB products such as partly due to the??oiling out?? phenomenon. The SURFONIC POA-L101 and POA-L61 surfactants can SURFONIC LF and P series products also show be used in soluble oils to promote solubilization of the lubricity effects above the cloud point. Careful selection oil in the concentrate. Under actual use conditions, of SURFONIC POA surfactants for a particular these products can act as defoamers and can boost application can give formulations with low foam, high lubricity, especially in the presence of a phosphate lubricity and high stability. ester. Higher HLB products will improve removal of the soluble oil formulation from parts and equipment. Forming Lubricants Semisynthetic Formulations In many forming operations it is possible to replace an oil-based lubricant with a simple synthetic formulation. SURFONIC POA-25R2 surfactant is an excellent choice This formulation might contain a SURFONIC POA for use in semisynthetic formulations. It will tend to copolymer, a phosphate ester for extreme pressure lower the foam of the system, promote good lubricity, activity and corrosion protection, and water. This type of and help to solubilize naphthenic oil and carboxylate formulation offers several advantages: the number of corrosion inhibitors. If fine particles are present in the parts that can be formed between die service is system, POA-25R2 can form a weak association with increased, the parts have better surface finish and the the particles and produce a thickening effect, which can formed parts are easier to clean. Many metalworking lead to reduced misting and??sling.?? operations using oil-based fluids can benefit from substitution with water-based synthetic formulations In semisynthetic formulations, SURFONIC POA-L61 and using the SURFONIC POA series of materials. POA-L101 surfactants offer reduced foam and improved lubricity. SURFONIC POA-L62 surfactant helps with wetting of metal parts. 36 Surfactants for the Metalworking Industry Table SURFONIC? POA Series Block Copolymers Falex Wear, 875 pounds Pour Specific Cloud Wetting Formulation A Formulation B Ross Miles Solubility? SURFONIC Appearance Point, Gravity, Viscosity, Point,??C Time1, Teeth Wear (T) Foam Height2, 100 SUS 100 SUS Teeth Wear Product at 25??C HLB??C 25/25??C cps, 25??C 1% aq. seconds Torque in-lbs (IP) mm, Initial/5 Min. Naphthenic Paraffinic Water Function POA-L61 Liquid T 6/0 I I D Defoamer for synthetic 22 IP and semisynthetic fluids. Lubricity enhancement.

26 POA-L62 Liquid T /10 I I S Active for cleaners. 24 IP Lubricity enhancement. POA-L62LF Liquid T 43/5.5 I I S Defoamer and lubricant 22 IP additive. POA-L101 Liquid T 0/0 I I S Solubilizer for semisynthetic 24 IP and synthetic fluids. POA-17R2 Liquid POA-25R2 Liquid T 57 0/0 I I S Lubricant in synthetic 22 IP fluids and solubilizer in semisynthetic fluids. 0.1% solution, 25??C 0.1% solution, 120??F 37.8??C Formulation A: 1% TEA, 1% SURFONIC PE-2258 phosphate ester, 1% SURFONIC POA surfactant, 97% Water. Formulation B: 0.17% TEA, 0.15% CORFREE? M-1 inhibitor, 0.07% DGA? Agent, 0.6% SURFONIC POA surfactant, 99% Water. 37 SECTION 3 Surfactants for the Metalworking Industry Linear Alcohol Ethoxylates?? SURFONIC? L Series Surfactants The SURFONIC? L series linear alcohol ethoxylates are Alcohol ethoxylates with or carbons and biodegradable, nonionic surfactants produced by the about 6 EO units are prime cleaning agents for addition of ethylene oxide to linear, primary alcohols. metalworking operations. Products in this range, like Their physical appearance at room temperature varies SURFONIC L12-6 surfactant, have the fastest surface from clear liquids to white waxy solids, depending on the dynamics; their nature allows them to migrate to and alcohol used and the degree of ethoxylation. The stabilize new surfaces quickly. This property is illustrated Huntsman line of linear alcohol ethoxylates is made from by the dynamic surface tension measurement (Figure alcohols containing only even carbon numbers in the 3.4). alkyl groups; the structure of these alcohols closely matches that of alcohols from natural sources. Alcohol ethoxylates with carbons and 7-12 moles Ethoxylates are made from a blend of the alcohol of EO are used in soluble oil and semisynthetic cutting homologues. It is possible to deduce the product fluids, particularly in paraffinic systems. Typically two composition from the product name; for instance, alcohol ethoxylates are used in a formulation to give a SURFONIC L24-3 surfactant is a blend of C12, C14 and wide range of good emulsification performance. Certain C16 linear alcohols reacted with three moles of ethylene pairs of surfactants compliment each other well in oxide. Properties of the SURFONIC L series products are emulsification applications. A blend of SURFONIC L24- listed in Table and SURFONIC L24-4 surfactants in a 1:2 ratio is often an optimal system. Higher EO products like The SURFONIC L series linear alcohol ethoxylates are SURFONIC L24-22 surfactant can be used to improve widely used as emulsifiers, cleaners, penetrants and the hard water tolerance of a formulation and can wetting agents in metalworking formulations. Appropriate improve the dispersibility of graphite or other particles in selection of the alcohol chain length and degree of a metal cleaning formulation. ethoxylation can provide the surfactant properties required for a particular application. At certain water/surfactant ratios, approximately in the 30-70% surfactant range, the alcohol ethoxylates Products with a short alcohol chain and low degree of exhibit a gel phase. In this range, an aqueous surfactant ethoxylation, such as SURFONIC L12-3 surfactant, are system will be a gel at room temperature but will good solubilization agents. In microemulsion cleaners and become an isotropic solution at temperatures above the