Identification and Evaluation of Hazardous Pyrolysates in Bio-Based Rigid Polyurethane-Polyisocyanurate Foam Smoke
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Methodology
3. Results and Discussion
3.1. Py-GC/MS Gaseous Product Characterization
3.2. Functional Group Assessment for the Volatile Organic Compounds
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Chemical Component | Structure |
---|---|
TOFA-based polyol [27], derived from: (1) oleic acid; (2) linoleic acid | |
Lupranol® 3422 (sorbitol-based polyether polyol) (BASF, Ludwigshafen, Germany) | (The exact chemical structure has not been disclosed) |
Solkane® 365/277 (86–92% of 1,1,1,3,3 pentafluorobutane; 8–14% of 1,1,1,2,3,3,3-heptafluoropropane) (Solvay Special Chemicals, Düsseldorf, Germany) | |
Water (deionized) | H2O |
Tertiary amine (Polycat® 5) N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDTA) (Evonik Industries, Essen, Germany) | |
30% potassium acetate in DEG (PC CAT TKA 30 and PC CAT Q 7-2) catalysts (Air Products Europe Chemicals B.V., Utrecht, The Netherlands) | |
Niax Silicone L-6915 (Momentive Performance Materials Inc., Geesthacht, Germany) | (The exact chemical structure has not been disclosed) |
Desmodur 44V20L (Covestro, Leverkusen, Germany; NCO content is 30.5–32.5 wt%) | |
Polyol Formulation (pbw) | ||
---|---|---|
Sample Code * | F_HF95 NCO 150 | F_HF95 NCO 300 |
NCO index | 150 | 300 |
TOFA-based polyol | 95.0 | 95.0 |
Lupranol 3422 | 5.0 | 5.0 |
Blowing reagent (water) | 0.5 | 0.5 |
Blowing agent (Solkane 365/277) | 40.0 | 70.0 |
Catalyst (Polycat 5) | 2.0 | 2.0 |
Catalyst (PC CAT TKA 30) | 1.5 | 2.5 |
Catalyst (PC CAT Q 7-2) | 2.0 | 2.0 |
Surfactant (L-6915) | 2.0 | 2.0 |
pMDI (Desmodur 44V20L) | 150.0 | 299.9 |
Characteristic | F_HF95 NCO 150 | F_HF95 NCO 300 |
---|---|---|
Start time, s | 20 | 20 |
String time, s | 37 | 75 |
Tack free time, s | 50 | 125 |
Temperature of polyol component before foaming, °C | 24 | 24 |
Apparent density of molded PU-PIR foams, kg/m3 | 31.6 | 35.6 |
Closed cell content, % | 93 | 96 |
Mc, g/mol | 499 | 549 |
Polyol moiety viscosity, mPa∙s | 62,560 ± 40 | 62,560 ± 40 |
No. | Peak Identification | Rt (Min) | Mrel NCO 150 (%) | Mrel NCO 300 (%) | Δ (%) | Rel. Δ (%) | GHS Hazard Statements |
---|---|---|---|---|---|---|---|
1 | Carbon dioxide | 5.287 | 6.65 | 6.02 | −0.63 | −9.5 | H280; H281 |
2 | 1-Butene | 5.405 | 0.14 | 0.09 | −0.05 | −35.7 | H220; H221; H280 |
3 | Phenoxyacetonitrile | 5.474 | 1.34 | 3.32 | 1.98 | 147.8 | H302; H312; H332 |
4 | cis-1,2-Dimethylcyclopropane | 5.575 | 1.25 | 0.49 | −0.76 | −60.8 | Not classified |
5 | Isoprene | 5.633 | 0.10 | 0.12 | 0.02 | 20.0 | H224; H341; H350; H412 |
6 | 3-Penten-1-yne | 5.826 | 0.11 | 0.07 | −0.04 | −36.4 | Not classified |
7 | 1-Hexene | 5.898 | 0.82 | 0.37 | −0.45 | −54.9 | H225; H304; H319 |
8 | Methyl isocyanide | 6.120 | 0.06 | trace | − | − | H302; H312; H332; H373 |
9 | 2-Butenal | 6.218 | 0.27 | 0.09 | −0.18 | −66.7 | H225; H301; H310; H311; H315; H318; H330; H335; H341; H373; H400 |
10 | 1-Heptene | 6.524 | 0.99 | 0.40 | −0.59 | −59.6 | H225; H304; H400; H410 |
11 | 1,2,5-Hexatriene | 6.641 | 0.30 | 0.12 | −0.18 | −60.0 | Not classified |
12 | Benzene | 6.767 | 0.32 | 0.21 | −0.11 | −34.4 | H225; H304; H315; H319; H340; H350; H372 |
13 | Tiglic aldehyde | 7.063 | 2.39 | 1.03 | −1.36 | −56.9 | H225; H315; H319; H335; H411 |
14 | 1-Octene | 7.583 | 1.16 | 0.40 | −0.76 | −65.5 | H225; H304; H315; H400; H410; H411 |
15 | Toluene | 8.029 | 0.81 | 0.96 | 0.15 | 18.5 | H225; H304; H315; H336; H361d; H373 |
16 | 2-Penten-1-ol, (E)- | 8.656 | 2.32 | 0.91 | −1.41 | −60.8 | H226 |
17 | M-Xylene | 9.581 | 0.23 | 0.16 | −0.07 | −30.4 | H226; H304; H312; H315; H318; H332 |
18 | P-Xylene | 9.736 | 0.45 | 0.37 | −0.08 | −17.8 | H226; H304; H312; H315; H319; H332; H335 |
19 | O-Xylene | 10.325 | 0.26 | 0.13 | −0.13 | −50.0 | H225; H226; H304; H312; H315; H319; H332; H335 |
20 | Styrene | 10.489 | 0.17 | 0.09 | −0.08 | −47.1 | H226; H315; H319; H332; H361d; H372 |
21 | 2-Heptanone | 10.859 | 0.27 | 0.11 | −0.16 | −59.3 | H226; H302; H332 |
22 | 1-Decene | 11.023 | 0.14 | 0.07 | −0.07 | −50.0 | H226; H304; H400; H410 |
23 | Propylbenzene | 11.367 | 0.11 | 0.06 | −0.05 | −45.5 | H226; H304; H335; H411 |
24 | 3-Ethyltoluene | 11.564 | 0.17 | 0.06 | −0.11 | −64.7 | H226; H304; H336; H411 |
25 | 1-Dodecene | 13.094 | 0.11 | 0.07 | −0.04 | −36.4 | H304; H315 |
26 | Butylbenzene | 13.509 | 0.12 | 0.04 | −0.08 | −66.7 | H226; H315; H319; H400; H410 |
27 | 2-Ethylhexanol | 13.864 | 0.38 | 0.18 | −0.20 | −52.6 | H315; H319; H332; H335 |
28 | Aniline | 14.278 | 3.99 | 4.68 | 0.69 | 17.3 | H301; H311; H317; H318; H331; H341; H351; H372; H400 |
29 | Benzonitrile | 14.439 | 0.05 | 0.07 | 0.02 | 40.0 | H302; H312 |
30 | Diethylene glycol | 15.264 | 0.31 | 0.44 | 0.13 | 41.9 | H302 |
31 | Pentylbenzene | 15.660 | 0.15 | 0.13 | −0.02 | −13.3 | H411; H412 |
32 | N-Methylaniline | 16.175 | 6.08 | 6.83 | 0.75 | 12.3 | H301; H311; H331; H373; H400; H410 |
33 | 2-Ethyl-2-methyl-1,3-propanediol | 16.708 | 0.64 | 0.16 | −0.48 | −75.0 | Not classified |
34 | Benzyl cyanide | 17.129 | 0.21 | 0.22 | 0.01 | 4.8 | H301; H302; H311; H330 |
35 | N-Methyl-m-toluidine | 17.554 | 0.22 | 0.09 | −0.13 | −59.1 | H301; H311 H331; H373; H412 |
36 | 2,5-Dimethylaniline | 17.925 | 0.39 | 0.20 | −0.19 | −48.7 | H301; H311; H331; H373; H411 |
37 | 2-Ethylaniline | 18.033 | 0.11 | 0.10 | −0.01 | −9.1 | H301; H302; H311; H319; H330; H331; H373; |
38 | cis-3-Tetradecene | 19.166 | 0.05 | 0.06 | 0.01 | 20.0 | Not classified |
39 | Carbazole | 19.606 | 0.55 | 0.15 | −0.40 | −72.7 | H315; H341; H351; H400; H411; H413 |
40 | 4-Vinylaniline | 20.090 | 0.16 | 0.11 | −0.05 | −31.3 | H302; H312; H315; H319; H332; H334; H335; H351; H373 |
41 | 7-Methylquinoline | 21.750 | 0.29 | 0.17 | −0.12 | −41.4 | H315; H318; H319; H335 |
42 | Indolizine | 22.136 | 0.05 | 0.10 | 0.05 | 100.0 | H315; H319 |
43 | 5H-Cyclopenta[b]pyridine | 22.431 | 0.10 | 0.16 | 0.06 | 60.0 | Not classified |
44 | Trimethylolpropane | 23.019 | 3.26 | 1.12 | −2.14 | −65.6 | Not classified |
45 | 4-Aminophenylacetonitrile | 23.831 | 0.11 | 0.22 | 0.11 | 100.0 | H302; H312; H315; H319; H332; H335 |
46 | 2,8-Dimethylquinoline | 24.018 | 0.31 | 0.17 | −0.14 | −45.2 | H302; H315; H318; H335 |
47 | Carbon monoxide | 24.167 | 0.44 | 0.16 | −0.28 | −63.6 | H220; H331; H360d; H372 |
48 | 8-Propylquinoline | 25.657 | 0.19 | 0.11 | −0.08 | −42.1 | Not classified |
49 | 1-Octadecene | 25.975 | 0.00 | 0.14 | 0.14 | 140.0 | H304 |
50 | Oxindole | 26.306 | 0.10 | 0.12 | 0.02 | 20.0 | Not classified |
51 | N-Methylacetanilide | 26.633 | 0.18 | 0.09 | −0.09 | −50.0 | H301 |
52 | Benzimidazole | 26.922 | 0.09 | 0.21 | 0.12 | 133.3 | H302; H315; H319; H335 |
53 | N-Formylindoline | 27.870 | 0.10 | 0.22 | 0.12 | 120.0 | Not classified |
54 | N-Methyldiphenylamine | 28.322 | 0.07 | 0.15 | 0.08 | 114.3 | H315; H319; H335 |
55 | 9-Octadecanone | 28.581 | 0.32 | 0.08 | −0.24 | −75.0 | Not classified |
56 | 4-Benzylaniline | 29.557 | 1.17 | 1.79 | 0.62 | 53.0 | H302; H312; H315; H319; H332; H335; |
57 | Acridine | 29.992 | 0.26 | 0.28 | 0.02 | 7.7 | H302; H315; H319; H335; |
58 | Acrolein | 30.767 | 0.14 | 0.21 | 0.07 | 50.0 | H225; H300; H311; H314; H330; H400; H410 |
59 | Phenol | 31.035 | 0.63 | 0.46 | −0.17 | −27.0 | H301; H311; H314; H331; H341; H373 |
60 | 1-Hexadecanol | 31.573 | 0.34 | 0.26 | −0.08 | −23.5 | H315; H319; H335; H400; H410; H411; H412; H413 |
61 | 9-Vinylcarbazole | 31.874 | 0.14 | 0.16 | 0.02 | 14.3 | H302; H312; H315; H317; H341; H400; H410 |
62 | Phenyl isocyanate | 32.398 | 0.25 | 0.20 | −0.05 | −20.0 | H226; H302; H314; H317; H318; H330; H334; H335; H400; H410; H411; H412 |
63 | 3,3′-Diaminodiphenylmethane | 35.723 | 4.89 | 6.31 | 1.42 | 29.0 | H302; H312; H315; H319; H332; H335; H351 |
64 | Methanol | 36.973 | 0.22 | 0.16 | −0.06 | −27.3 | H225; H301; H311; H331; H370 |
65 | 4,4′-Methylenedianiline | 38.071 | 45.26 | 52.41 | 7.15 | 15.8 | H317; H341; H350; H370; H373; H411 |
66 | Nitric oxide | 38.503 | 0.89 | 0.58 | −0.31 | −34.8 | H270; H280; H314; H318; H330; H331; H373 |
67 | Ammonia | 38.813 | 0.61 | 0.89 | 0.28 | 45.9 | H221; H314; H331; H400 |
68 | Water | 39.136 | 4.67 | 3.46 | −1.21 | −25.9 | Not classified |
69 | Nitrogen dioxide | 40.054 | 0.73 | 0.44 | −0.29 | −39.7 | H270; H280; H314; H318; H330 |
Functional Group/Bond | Counts | Examples |
---|---|---|
Alkene | 38 | 1-Butene, Isoprene, 1-Hexene, 1-Dodecene |
Alkene incorporated in benzene ring structure | 21 | M-Xylene, P-Xylene, O-Xylene, 3-Ethyltoluene, 9-Vinylcarbazole, Carbazole |
Alkyne | 1 | 3-Penten-1-yne |
Phenyl | 19 | 4,4′-Methylenedianiline, N-Methyldiphenylamine |
Amine | 20 | Aniline, N-Methylaniline, 2,5-Dimethylaniline |
Alcohol | 8 | 2-Ethylhexanol, Trimethylolpropane, Diethylene glycol |
Ether | 1 | Diethylene glycol |
Aldehyde | 4 | 2-Butenal, Tiglic aldehyde, N-Formylindoline, Acrolein |
Ketone | 2 | 2-Heptanone, 9-Octadecanone |
Amide | 2 | N-Methylacetanilide, Oxindole |
Isocyanide | 1 | Methyl isocyanide |
Isocyanate | 1 | Phenyl isocyanate |
Nitrile | 4 | Benzyl cyanide, Benzonitrile, Phenoxyacetonitrile |
GHS Hazard | H Code | Phrase | Compounds with H Code | Fraction of all Pyrolysis Products (%) |
---|---|---|---|---|
Physical hazards | H220 | Extremely flammable gas | 2 | 3 |
H221 | Flammable gas | 2 | 3 | |
H224 | Extremely flammable liquid and vapor | 1 | 1 | |
H225 | Highly flammable liquid and vapor | 10 | 14 | |
H226 | Flammable liquid and vapor | 11 | 16 | |
H270 | May cause or intensify fire; oxidizer | 2 | 3 | |
H280 | Contains gas under pressure; may explode if heated | 4 | 6 | |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury | 1 | 1 | |
Health hazards | H301 | Toxic if swallowed | 10 | 14 |
H302 | Harmful if swallowed | 16 | 23 | |
H304 | May be fatal if swallowed and enters airways | 13 | 19 | |
H310 | Fatal in contact with skin | 1 | 1 | |
H311 | Toxic in contact with skin | 10 | 14 | |
H312 | Harmful in contact with skin | 11 | 16 | |
H314 | Causes severe skin burns and eye damage | 6 | 9 | |
H315 | Causes skin irritation | 25 | 36 | |
H317 | May cause an allergic skin reaction | 4 | 6 | |
H318 | Causes serious eye damage | 8 | 12 | |
H319 | Causes serious eye irritation | 19 | 28 | |
H330 | Fatal if inhaled | 7 | 10 | |
H331 | Toxic if inhaled | 10 | 14 | |
H332 | Harmful if inhaled | 12 | 17 | |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled | 2 | 3 | |
H335 | May cause respiratory irritation | 17 | 25 | |
H336 | May cause drowsiness or dizziness | 2 | 3 | |
H340 | May cause genetic defects | 1 | 1 | |
H341 | Suspected of causing genetic defects | 7 | 10 | |
H350 | May cause cancer | 3 | 4 | |
H351 | Suspected of causing cancer | 4 | 6 | |
H361d | Suspected of damaging the unborn child | 2 | 3 | |
H370 | Causes damage to organs | 2 | 3 | |
H372 | Causes damage to organs through prolonged or repeated exposure | 4 | 6 | |
H373 | May cause damage to organs through prolonged or repeated exposure | 11 | 16 | |
Environmental hazards | H400 | Very toxic to aquatic life | 13 | 19 |
H410 | Very toxic to aquatic life with long-lasting effects | 9 | 13 | |
H411 | Toxic to aquatic life with long-lasting effects | 10 | 14 | |
H412 | Harmful to aquatic life with long-lasting effects | 5 | 7 | |
H413 | May cause long-lasting harmful effects to aquatic life | 2 | 3 | |
Not classified | - | - | 12 | 17 |
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Reinerte, S.; Jurkjane, V.; Cabulis, U.; Viksna, A. Identification and Evaluation of Hazardous Pyrolysates in Bio-Based Rigid Polyurethane-Polyisocyanurate Foam Smoke. Polymers 2021, 13, 3205. https://doi.org/10.3390/polym13193205
Reinerte S, Jurkjane V, Cabulis U, Viksna A. Identification and Evaluation of Hazardous Pyrolysates in Bio-Based Rigid Polyurethane-Polyisocyanurate Foam Smoke. Polymers. 2021; 13(19):3205. https://doi.org/10.3390/polym13193205
Chicago/Turabian StyleReinerte, Sanita, Vilhelmine Jurkjane, Ugis Cabulis, and Arturs Viksna. 2021. "Identification and Evaluation of Hazardous Pyrolysates in Bio-Based Rigid Polyurethane-Polyisocyanurate Foam Smoke" Polymers 13, no. 19: 3205. https://doi.org/10.3390/polym13193205