High-solids polyester resins for pplince nd generl metl cotings Bsed on NPG glycol; 1,4-CHDA; purified isophthlic cid (PIA); nd purified terephthlic cid (PTA) CH 3 H CH 2 C CH 2 H H H CH 3 NPG glycol 2,2-dimethyl-1,3-propnediol CAS 126-30-7 PIA Purified isophthlic cid CAS 121-91-5 H C C H H H 1,4-CHDA 1,4-cyclohexnedicrboxylic cid CAS 1076-97-7 PTA Purified terephthlic cid CAS 100-21-0 Strting point formultions HS-3-1NCp nd HS-3-2NCp
High-solids polyester resins for pplince nd generl metl cotings Bsed on NPG glycol; 1,4-CHDA; purified isophthlic cid (PIA); nd purified terephthlic cid (PTA) (Continued) Resin formultion HS-3-1NCp HS-3-2NCp Component Equivlents Moles Grms Stge 1 NPG glycol 14.85 7.42 773 773 Phthlic nhydride 4.03 2.02 299 purified isophthlic cid (PIA) 3.02 1.51 2.51 purified terephthlic cid (PTA) 1.01 0.50 84 Stge 2 Trimethylolpropne 0.59 0.20 26 26 1,4-CHDA 6.05 3.02 521 521 Stge 3 Trimethylolpropne 0.59 0.20 26 26 Totl chrge 1,645 1,681 Theoreticl distillte 145 181 Theoreticl yield 1,500 1,500 No ctlyst or stbilizer Nitrogen flow: dequte to mintin <1% oxygen Processing procedure Stge 1 Chrge ll stge 1 rectnts to 2-L rection kettle equipped with heting mntle, gittor, nitrogen blnket, thermocouple, prtil condenser, wter trp, nd totl condenser. 1 Het to 220 C (428 F) over 3 hours. Mintin t 220 C (428 F) until n cid number of 5 (mg KH/g resin) or less is obtined, typiclly n dditionl 2 hours. The distillte t the end of this step will be pproximtely 34 ml for HS-3-1NCp nd 68 ml for HS-3-2NCp. Stge 2 After cooling to 140 C (284 F) or less, dd stge 2 rectnts. Het to 220 C (428 F) nd mintin until one-hlf of the theoreticl distillte is collected for this stge. The totl distillte t the end of this step will be pproximtely 73 ml for HS-3-1NCp nd 90 ml for HS-3-2NCp. This step normlly requires 30 to 60 minutes. Stge 3 2 After cooling to 140 C (284 F) or less, dd third-stge TMP chrge. Het to 220 C (428 F) nd mintin until n cid number of 10 ± 1 (mg KH/g resin) is obtined. This step requires 2 hours. The totl distillte t this step will be pproximtely 120 ml for HS-3-1NCp nd 154 ml for HS-3-2NCp. After cooling to 140 C (284 F) or less, dd solvent. 1 Refer to publiction N-345, Processing polyester resins for cotings pplictions. 2 It my be possible to two-stge these resins (combine the first nd second stges), but this hs not been investigted. Previous work in Technicl Service nd Development lbortories hs shown tht two-stging the TMP brncher is beneficil. More informtion on this subject is vilble in publiction N-305, Polyester resin synthesis techniques for chieving lower VC nd improving coting performnce. 2
High-solids polyester resins for pplince nd generl metl cotings Bsed on NPG glycol; 1,4-CHDA; purified isophthlic cid (PIA); nd purified terephthlic cid (PTA) (Continued) Resin properties HS-3-1NCp HS-3-2NCp Equivlents of H/equivlents of CH (R vlue) 1.59 1.59 Trget cid number, mg KH/g resin 10 10 Clculted hydroxyl number, mg KH/g resin 222 222 Moleculr weight, M n 840 960 Cone nd plte viscosity @ 100 C, P s (P) 0.57 (5.7) 0.78 (7.8) Grdner-Holdt viscosity, 85% solids in xylene Z 4 Z 5 Dys to hzing t room temperture >180 105 Moleculr weight determined using GPC with refrctive index detector. Enmel formultion Ingredient Wt% Polyester resin (85 wt% in xylene) 45.0 Cymel 303 melmine resin 12.0 Ti-Pure R-900 Ti 2 33.0 p-toluenesulfonic cid ctlyst (40 wt% in i-propnol) 0.3 Fluorosurfctnt dditive (20 wt% in EEP) 0.5 Solvent blend 9.2 100.0 Pigment:binder rtio 40:60 Polyester:melmine rtio 75:25 Additionl solvent blend ws dded to ech enmel to obtin #4 Ford Cup viscosity of 30 seconds. MAK/ EEP/n-butyl lcohol in 70:15:15 rtio. Enmel properties HS-3-1NCp HS-3-2NCp Determined density, g/l (lb/gl) 1,356 (11.31) 1,344 (11.21) Nonvoltiles, wt% Clculted 79 78 Determined 20 min @ 177 C (350 F) 74.0 72.4 90 min @ 110 C (230 F) 76.6 75.2 Determined VC, wt VC/vol coting 20 min @ 177 C (350 F), g/l (lb/gl) 342 (2.85) 357 (2.98) 90 min @ 110 C (230 F), g/l (lb/gl) 316 (2.64) 334 (2.79) VC temperture conditions suggested in the My 25, 1988, issue of Chemicl Week s EPA Reference Method 24. 3
High-solids polyester resins for pplince nd generl metl cotings Bsed on NPG glycol; 1,4-CHDA; purified isophthlic cid (PIA); nd purified terephthlic cid (PTA) (Continued) Cured film properties HS-3-1NCp HS-3-2NCp Film thickness, mils (microns) 1.8 (45.7) 1.9 (48.3) Gloss 60 /20 91/ 80 91/ 80 Solvent resistnce, MEK double rub b 200+ 200+ Flexibility/hrdness 3.2-mm ( 1 8-in.) Conicl mndrel flexibility, % pss 100 100 Impct resistnce Direct, N m (in.-lb) 13.1 (116) 13.1 (116) Reverse, N m (in.-lb) 5.0 (44) 6.8 (60) Pencil hrdness, mr 4H 4H Stin resistnce, covered/uncovered c,d Iodine fter 30 min 4/4 3/4 Mustrd fter 24 h 5/5 5/5 Lipstick fter 24 h 5/5 5/5 Ink fter 24 h 5/5 4/5 Ketchup fter 24 h 5/5 5/5 Grpe juice fter 24 h 5/5 5/5 Chemicl resistnce, covered/uncovered c,d 50% NH solution fter 8 h 5/5 5/5 50% Sulfuric cid solution fter 8 h 2/2 2/2 Moisture resistnce Clevelnd humidity fter 1,000 h @ 60 C (140 F) % Gloss retention @ 60 /20 99/95 100/100 Blistering d 5 5 Slt spry fter 1,000 h Creepge, mm (in.) 1.59 (0.0625) 1.59 (0.0625) Blistering d 5 5 Crcking d 5 5 Detergent resistnce fter 10 d @ 74 C (165 F) e Creepge, mm (in.) 4.76 (0.1875) 3.18 (0.125) % Gloss retention @ 60 /20 99/84 97/84 Blistering d 4 3 Crcking d 4 5 Enmels were spryed on 20-guge cold-rolled Bonderite 37 pretreted steel test pnels nd cured for 20 minutes t 177 C (350 F). b 200 double rubs with MEK, quickly wiped dry. Pss = no thumbnil mr. c The stin nd chemicl resistnce pnels were wshed with Dwn dishwshing detergent, rinsed with wter, nd wiped dry before evlution. d Scle: 5 = no effect, 4 = slight effect, 3 = moderte effect, 2 = considerble effect, nd 1 = severe effect. e The test environment from ASTM Method D2248-73 ws used. 4
High-solids polyester resins for pplince nd generl metl cotings Bsed on NPG glycol; 1,4-CHDA; purified isophthlic cid (PIA); nd purified terephthlic cid (PTA) (Continued) Formultion comprison summry HS-3-1NCp HS-3-2NCp verll similr coting performnce Lower viscosity Lower VC More comptible with xylene More flexible Better moisture resistnce Rw mteril suppliers n-butyl lcohol Cymel 303 melmine resin 1,4-CHDA EEP b purified isophthlic cid (PIA) MAK NPG glycol Phthlic nhydride purified terephthlic cid (PTA) Ti-Pure R-900 Ti 2 Trimethylolpropne p-toluenesulfonic cid ctlyst 1,4-Cyclohexnedicrboxylic cid Cytec Stepn DuPont Geo Specilties, Perstorp Aldrich b Ethyl 3-ethoxypropionte 5
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