The JEFFAMINE Polyetheramines - Huntsman …

1 The JEFFAMINE Polyetheramines JEFFAMINE polytheramines are a part of an JEFFAMINE DIAMINES. expanding family of Huntsman products. They (D, ED, and EDR series). contain primary amino groups attached to the end JEFFAMINE diamines include the D, ED, and of a polyether backbone. The polyether backbone EDR series products. The D signifies a diamine, is normally based on either propylene oxide (PO), ED signifies a diamine with a predominately PEG. ethylene oxide (EO), or mixed PO/EO. Thus they backbone, and EDR designates a highly reactive, are called Polyetheramines . Historically, the PEG based diamine.

2 As with the M series, the JEFFAMINE polyetheramine family consisted of number represents the approximate molecular monoamines, diamines, and triamines based on weight. this core structure. Recently, the addition of secondary, hindered, high-conversion, and JEFFAMINE D Series polytetramethylene glycol (PTMEG) based JEFFAMINE D series products are amine Polyetheramines has increased the utility of this terminated PPGs with the following representative unique product range. The JEFFAMINE . structure: Polyetheramines undergo typical amine reactions, often imparting increased flexibility, toughness, low viscosity, and low color.

3 The wide range of molecular weight, amine functionality, repeating H2N ( O. ) NH2. unit type, and distribution can provide flexibility in x the design of new compounds or mixtures. CH3 CH3. JEFFAMINE MONOAMINES (M series). JEFFAMINE monoamines are designated as JEFFAMINE x MW*. the JEFFAMINE M series. The letter M signifies a D-230 ~ 230. monoamine and the number represents the D-400 ~ 430. approximate molecular weight. D-2000 ~33 2,000. JEFFAMINE M series products are prepared D-4000 (XTJ-510) ~68 4,000. by reaction of a mono-alcohol initiator with EO. and/or PO, followed by conversion of the resulting JEFFAMINE ED Series terminal hydroxyl groups to amines.

4 M series JEFFAMINE ED series products are polyether products have the following representative diamines based on a predominantly PEG. structure: backbone. PEG imparts complete water solubility to each of the products in this series. The O NH2 JEFFAMINE ED products have the following H3C O representative structure: x y R H2N. ( ) (O ) (O ) NH2. O. x y z R= H for (EO), or CH3 for (PO) CH3 CH3 CH3. JEFFAMINE PO/EO mol ratio MW* JEFFAMINE y x+z MW*. M-600 (XTJ-505) 9/1 600 HK-511 ~ 220. M-1000 (XTJ-506) 3/19 1,000 ED-600 (XTJ-500) ~ ~ 600. M-2005 29/6 2,000 ED-900 (XTJ-501) ~ ~ 900.

5 M-2070 10/31 2,000 ED-2003 (XTJ-502) ~39 ~ 2,000. * MW = approximate molecular weight JEFFAMINE EDR Series JEFFAMINE M-600 and JEFFAMINE M-2005 JEFFAMINE EDR-148 (XTJ-504) and Polyetheramines are predominately polypropylene JEFFAMINE EDR-176 (XTJ-590) amines are much glycol (PPG) based, whereas JEFFAMINE M-1000 more reactive than the other JEFFAMINE diamines and JEFFAMINE M-2070 Polyetheramines are and triamines. They are represented by the predominately polyethylene glycol (PEG) based following structure: and are therefore more hydrophilic. JEFFAMINE Base product MW*. H2N.

6 (CH2) O. O. ( CH2) NH SD-231 (XTJ-584) D-230 315. x 2 SD-401 (XTJ-585) D-400 515. x SD-2001 (XTJ-576) D-2000 2050. ST-404 (XTJ-586) T-403 565. JEFFAMINE x MW. EDR-148 (XTJ-504) 148 EXPERIMENTAL AMINES. EDR-176 (XTJ-590) 176 This next series of amines includes monofunctional amines similar to the M series. These products can be used in a number of They are oleophilic and not water soluble. applications since they are unhindered diamines miscible in a wide variety of solvents. Reactions XTJ-435 Chemical Intermediate typical of aliphatic diamines (polyamide formation through reaction with dibasic acids, epoxy resin CH3.)

7 Curing, polyurea formation through reaction with isocyanates) may be expected with these products. H3C. ( CH2 ) O. NH2. 12 O.. JEFFAMINE TRIAMINES (T series) CH3. JEFFAMINE T series products are triamines prepared by reaction of PO with a triol initiator, XTJ-435 is a monoamine derived from a PO. followed by amination of the terminal hydroxyl adduct of a C12-14 alcohol. This product is groups. They are exemplified by the following restricted and may only be used as a chemical structure: intermediate. CH 3 XTJ-436. ( H2C ). (O ) CH3. y NH 2. n C 9H19. H2N. ( ) (O ) NH 2 (O ) NH2.

8 O x z CH 3 R CH 3. Moles PO XTJ-436 is a 1000 molecular weight, JEFFAMINE R n (x+y+z) MW* nonylphenol initiated, polypropylene glycol derived T-403 C2H5 1 5-6 440 monoamine. T-3000 (XTJ-509) H 0 50 3000. T-5000 H 0 85 5000 Slower Amines Slower amines analogous to JEFFAMINE D- 230 and JEFFAMINE T-403 Polyetheramines are JEFFAMINE Secondary Amines now available under the names XTJ-568 and XTJ- 566, respectively. These unique materials are (SD Series, ST Series) primary amines created by amination of butylene The SD Series and ST Series products consist oxide (BO) capped alcohols.

9 This method results in of secondary amine versions of the JEFFAMINE . primary amines with the terminal end group core products. The SD signifies a secondary structure represented below: diamine and ST signifies a secondary triamine. The amine end-groups are reacted with a ketone ( NH2. acetone) and reduced to create hindered secondary amine end groups represented by the following terminal structure: CH3. H3C NH. Higher Conversion Amines Methods have been developed to increase CH3 CH3 functionality and conversion to primary amines for several of the core JEFFAMINE Polyetheramines .

10 One reactive hydrogen on each end group Two such products are currently available: a high provides for more selective reactivity and makes conversion 440 molecular weight diamine (XTJ- these secondary di- and triamines useful for 582), and a high conversion 2000 molecular weight intermediate synthesis and intrinsically slower diamine (XTJ-578). The higher functionality and reactivity compared with the primary JEFFAMINE conversion are beneficial in polymerizations such amines. as polyamide formation. JEFFAMINE Polyetheramine Properties Typical Properties Sales Specifications JEFFAMINE product Avg.