Multi-Analytical Assessment of Bodied Drying Oil Varnishes and Their Use as Binders in Armour Paints
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Sample Overview
Application of Liquid Oils and Varnishes to Steel Sheet Substrate
2.2. Ageing Conditions
2.3. Investigations and Analytical Methods
2.3.1. Testing Chemical and Physical Properties of the Oils
2.3.2. Fourier-Transform Infrared Spectroscopy
2.3.3. Gas Chromatography–Mass Spectrometry
2.3.4. Water Immersion Test
3. Results and Discussion
3.1. Liquid Samples
3.1.1. Chemical and Physical Properties of Liquid Oils and Varnishes
3.1.2. FTIR
3.1.3. GC-MS
- -
- OH-L shows the typical fatty acid profile of linseed oil, corroborated by a P/S ratio of 1.7; all special fatty acids were found in this formulation;
- -
- WHT-L, which, similarly to stand oil, was found to contain cyclic compounds, also contained castor oil, as indicated by the identification of its marker (i.e., ricinoleic acid—mass spectrum in Figure 2c). This non-drying oil can be found in modern commercial artist oil formulations as an adulterant in linseed oil or added for rheological purposes [29]. Castor oil is made into a drying oil by dehydration through the formation of an unsaturated hydroxy fatty acid [6]. In raw and blown form it serves as a plasticiser in coatings. In hydrated form, castor oil improves the elasticity, water resistance, alkali resistance and colour retention of paint, similar to tung oil. Its presence likely influenced the final P/S ratio of the mixture, which was 1.2. Indeed, castor oil’s P/S ratio is generally around 1, while linseed oil has a P/S ratio ranging from 1.3 to 1.8 [30];
- -
- WS-L contains a special monounsaturated fatty acid, namely erucic acid (mass spectrum in Figure 2d), which is considered as the biomarker for seeds of the Brassicaceae family, such as rapeseed. Rapeseed oil is a semi-drying oil that was introduced in the 20th century as a lubricant and/or as an adulterant in linseed oils [29,31]. Again, the presence of a mixture of different oils could have slightly modified the P/S ratio, which was 1.2;
- -
- The mixture containing WHT-L and tung oil did not contain any additional oils and presented a P/S ratio of 1.2.
3.2. Solid Samples
3.2.1. Artificial Ageing
3.2.2. Water Immersion Test
3.2.3. FTIR
3.2.4. GC-MS
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Appendix A. Chemical and Physical Properties of the Paint Binders
Measured Property/Characteristic | Results on Commercial Binders | |||||||
Methodological Details | OH-L | WHT-L | WS-L | T-L | ||||
Method | Unit/at | At | Uncert., % | |||||
Density | Electronic | g/cm3 | 20 °C | - | 0.9339 | 0.9370 | 0.9575 | 0.9391 |
Refractive index | Automatic | - | 20 °C | ±0.01 | 1.4826 | 1.4823 | 1.4907 | 1.5194 |
60 °C | ±0.01 | 1.4682 | 1.4679 | 1.4763 | >1.5000 | |||
Cold test | AAK method | - | 6 h | - | 2 | 2 | 2 | 2 |
Insoluble impurities | AOCS Ca 3a-46 | % | 20 | <0.01 | 0.01 | <0.01 | <0.01 | |
Alkaline impurities | EP 2.4.19 | Ml | - | 0.15 | <0.10 | <0.10 | <0.10 | |
Water content | AOCS CA 2E-84 | % | ±15 | 0.06 | 0.1 | 0.03 | 0.04 | |
Iodine value | AOCS Cd 1c-85 + ISO 3961 | mg iodine/100 g | - | 196 | 177 | 112 | 161 | |
Saponification value | IUPAC 2.202 | mg KOH/g | ±2 | 188 | 191 | 192 | 192 | |
Free fatty acids | IUPAC 2.201 (m) | - | 282 | ±3 | 0.94 | 1.7 | 3.1 | 1.7 |
Acid value | IUPAC 2.201 (m) | mg KOH/g | ±3 | 1.87 | 3.41 | 6.24 | 3.3 | |
Peroxide value | AOCS Cd 8-53 | meq/kg | ±15 | 2.6 | 6 | 3.3 | 5.6 | |
Colour (Lovibond) | AOCS Cc 13j-97 | Yellow | ±25 | 130.0 | 140.0 | 40.0 | 60.0 | |
Red | 20.0 | 14.0 | 3.0 | 7.0 | ||||
Blue | 0.0 | 0.0 | 0.0 | 0.0 | ||||
Total | 330.0 | 280.0 | 70.0 | 130.0 |
- European Pharmacopeia Commission. Alkaline impurities in fatty oils. Methods of analysis EP 2.4.19; EU): European Pharmacopeia Commission: Strasbourg, Germany, 2005.
- International Organization for Standardization. (2018). Animal and vegetable fats and oils. Determination of iodine value. (ISO 3961:2018); International Organization for Standardization: Geneva, Switzerland, 2018
- IUPAC (1992). Determination of the saponification value (S.V). Standard Methods for the Analysis of Oils, Fats and Derivatives. IUPAC 2.202:1992; Oxford, United Kingdom: International Union of Pure and Applied Chemistry Commission on Oils, Fats and Derivatives, 1992.
- IUPAC (1992). Determination of the acidity of lecithins. Standard Methods for the Analysis of Oils, Fats and Derivatives. IUPAC 2.201/ (5.201); Oxford, United Kingdom: International Union of Pure and Applied Chemistry Commission on Oils, Fats and Derivatives, 1992.
- IUPAC (1992). Capillary column gas—liquid chromatography of fatty acid methyl esters. Standard Methods for the Analysis of Oils, Fats and Derivatives. IUAPAC 2.304:1992; Oxford, United Kingdom: International Union of Pure and Applied Chemistry Commission on Oils, Fats and Derivatives, 1992.
- AOCS (2017). Moisture. Karl Fischer Method. AOCS Official Method Ca 2e-84, revised 2017. Urbana, USA: The American Oil Chemists’ Society, 2017.
- AOCS (2017). Calculated Iodine Value. AOCS Official Method AOCS Cd 1c-85, revised 2017; Urbana, USA: The American Oil Chemists’ Society, 2017.
- AOCS (2003). Peroxide Value—Acetic Acid-Chloroform Method. AOCS Official Method AOCS Cd 8-53 (1953/revised 2003); Urbana, USA: The American Oil Chemists’ Society, 2003.
- AOCS (2017). Insoluble Impurities in Fats and Oil. AOCS Official Method AOCS Ca 3a-46, revised 2017; Urbana, USA:. The American Oil Chemists’ Society, 2017.
- AOCS (2017). Color of Fats and Oils, Automated Method. AOCS Official Method AOCS Cc 13j-97, revised 2017; Urbana, USA. The American Oil Chemists’ Society, 2017.
Appendix B. GC-MS Results
RT (min) | Identified Compound | OH | WHT | WS | WT | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
OH-L | OH-0 | OH-1 | OH-2 | WHT-L | WHT-0 | WHT-1 | WHT-2 | WS-L | WS-0 | WS-1 | WS-2 | WT-L | WT-0 | WT-1 | WT-2 | ||
9.412 | Pimelic acid, dimethyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
9.784 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
10.165 | Octanoic acid, 8-hydroxy-, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
10.342 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
10.580 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
10.652 | Nonanoic acid, 9-oxo-, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
10.767 | Suberic acid, dimethyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
11.053 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
11.692 | Decanoic acid, 9-oxo-, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
12.063 | Azelaic acid, dimethyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
13.196 | Sebacic acid, dimethyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
14.005 | Myristic acid methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
15.573 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
16.131 | Palmitic acid, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
16.172 | Glycerol derivative | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
16.934 | Undecanedioic acid, 4-oxo-, dimethyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
17.801 | Oleic acid methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
18.036 | Stearic acid methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||||
18.206 | Linoleic acid methyl ester | √ | √ | √ | √ | √ | |||||||||||
18.399 | Linolenic acid methyl ester | √ | √ | √ | |||||||||||||
18.920 | Nonadecanoic acid, methyl ester (internal standard) | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ |
19.210 | Alpha-eleostearic acid methyl ester | √ | |||||||||||||||
19.570 | Ricinoleic acid methyl ester | √ | √ | √ | √ | ||||||||||||
19.624 | Octadecanoic acid, 10-oxo-, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
19.767 | Arachidic acid methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
19.803 | 7-(o-pentylphenyl)-heptanoic acid methyl ester | √ | √ | √ | |||||||||||||
19.883 | 9-(o-propylphenyl)-nonanoic acid methyl ester | √ | √ | √ | |||||||||||||
19.944 | Glycerol (main) | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | |
21.196 | Erucid acid methyl ester | √ | √ | √ | √ | ||||||||||||
21.386 | Behenic acid, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
22.712 | Octadecanoic acid, 9,10-epoxy | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
22.885 | Tetracosanoic acid, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
24.287 | Hexacosanoic acid, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
24.817 | β-Monolinolein | √ | √ | √ | |||||||||||||
24.875 | Octadecanoic acid, 9,10-oxo-, methyl ester | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | ||||
24.889 | Linolenic acid 1,3-dimethoxypropan-2-yl ester | √ | √ | √ | |||||||||||||
24.930 | Linolenic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester (Z,Z,Z)- | √ | √ | √ | |||||||||||||
25.561 | Sitosterol | √ |
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Typology (Drying Oil Used) | Paint Name | Description | Exposure |
---|---|---|---|
OH Air-blown linseed oil varnish (heated to 130–150 °C, drier: Co-Zr ethyl hexane/octate/proprionate). | OH-L | Liquid | Fresh oil |
OH-0 | Solid film—unaged | 4 weeks naturally aged | |
OH-A1 | Solid film—aged 1 | 64 kJ | |
OH-A2 | Solid film—aged 2 | 97 kJ | |
WHT Heat-bodied manganese compound varnish (boiled at high temperature, 280 °C). | WHT-L | Liquid | Fresh oil |
WHT-0 | Solid film—unaged | ||
WHT-A1 | Solid film—aged 1 | 64 kJ | |
WHT-A2 | Solid film—aged 2 | 97 kJ | |
WS Stand oil—linseed stand oil, 50 dPa·s | WS-L | Liquid | Fresh oil |
WS-0 | Solid film—unaged | ||
WS-A1 | Solid film—aged 1 | 64 kJ | |
WS-A2 | Solid film—aged 2 | 97 kJ | |
WT 80 wt% WHT + 20 wt% bodied tung oil | WT-L | Liquid | Fresh oil |
WT-0 | Solid film—unaged | ||
WT-A1 | Solid film—aged 1 | 64 kJ | |
WT-A2 | Solid film—aged 2 | 97 kJ | |
T Bodied tung oil | T | Liquid | For chemical and physical quantification only |
L | L-0 | Unaged | Litharge varnish * |
P | P-0 | Unaged | Pyrolusite varnish * |
MB | MB-0 | Unaged | Manganese borate varnish * |
OHT | OHT-0 | Unaged | OH with 20 wt% tung oil * |
Assignment | Linseed Oils | OH-L | WHT-L | WS-L | Tung Oils | T-L |
---|---|---|---|---|---|---|
ν (O-H) | ||||||
3067 | 3451 | |||||
-/3340 | 3047 | |||||
ν (C-H) in C=C-H | 3008/- | 3010 | 3010 | 3012 | 3013 | |
3006 | ||||||
ν (C-H) | 2954 sh/overlapped | 2956 | 2954 | 2953 | ||
ν (C-H) | 2924 | 2924 | 2923 | 2922 | 2932/2927 | 2924 |
ν (C-H) | 2852 | 2853 | 2853 | 2853 | ||
ν (C=O) | 1744/1740 | 1743 | 1742 | 1742 | 1745/1740 | 1741 |
ν (C=C) | 1652/1634 sh | 1654 | 1654 | 1656 | 1642 | 1642 |
1587 | 1586 | |||||
1521 | ||||||
δ (C-H) in methyl | 1461/1462 | 1460 | 1460 | 1459 | 1464/1461 | 1459 |
δ (C-H) in methylene | 1418/1416 | 1418 | 1418 | 1418 | 1416/1415 | |
δ (C-H) in methyl | 1375 | 1376 | 1376 | 1376 | 1376/1377 | 1377 |
ν (C-O) in C-O-C in esters | 1238/1240 | 1237 | 1238 | 1235 | 1238/1240 | 1237 |
ν (C-O) in C-O-C in esters | 1163/1165 | 1160 | 1160 | 1159 | 1159 | |
1119 | ||||||
ν (C-O) in C-O-C in esters | 1099 | 1099 | 1098 | 1099 | 1100 | 1099 |
1069 | 1069 | |||||
1028 | 1029 | |||||
992 | 990 | |||||
987 | 987 | 975 | ||||
ω (CH) in CH=CH wagging isolated trans | -/971 | 969 | 970 | 967 | 965 | 964 |
914 | 914 | |||||
872 | ||||||
852 | ||||||
807 | ||||||
866 | 867 | |||||
791 | 792 | |||||
δ/CH2) rocking | -/720 | 721 | 721 | 722 | 728 | 726 |
OH-0 | WHT-0 | WS-0 | WT-0 | OHT-0 | L-0 | P-0 | MB-0 | |
---|---|---|---|---|---|---|---|---|
Milky time | 1.5 h | 1.5 h | >24 h | >24 h | >24 h | >24 h | 1.5 h | ~16 h |
Comments | White | White | * | * | * | * | White | Somewhat frosty appearance |
Molar Ratios | OH | WHT | WS | WT | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
OH-0 | OH-A1 | OH-A2 | WHT-0 | WHT-A1 | WHT-A2 | WS-0 | WS-A1 | WS-A2 | WT-0 | WT-A1 | WT-A2 | |
P/S | 1.73 | 1.70 | 1.73 | 1.24 | 1.24 | 1.20 | 1.17 | 1.19 | 1.18 | 1.15 | 1.26 | 1.24 |
A/P | 1.64 | 1.90 | 1.97 | 0.76 | 2.03 | 1.50 | 0.60 | 0.70 | 0.54 | 1.82 | 1.60 | 1.62 |
D/P | 2.18 | 2.47 | 2.52 | 1.21 | 2.67 | 1.92 | 0.97 | 1.18 | 0.87 | 2.63 | 2.30 | 2.26 |
O/S | 0.17 | 0.12 | 0.08 | 0.12 | 0.09 | 0.05 | 0.30 | 0.10 | 0.52 | 0.09 | 0.08 | 0.07 |
%D | 42.86 | 47.03 | 47.30 | 28.85 | 48.63 | 47.33 | 23.82 | 27.46 | 21.09 | 44.26 | 43.74 | 43.05 |
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Izzo, F.C.; Källbom, A.; Nevin, A. Multi-Analytical Assessment of Bodied Drying Oil Varnishes and Their Use as Binders in Armour Paints. Heritage 2021, 4, 3402-3420. https://0-doi-org.brum.beds.ac.uk/10.3390/heritage4040189
Izzo FC, Källbom A, Nevin A. Multi-Analytical Assessment of Bodied Drying Oil Varnishes and Their Use as Binders in Armour Paints. Heritage. 2021; 4(4):3402-3420. https://0-doi-org.brum.beds.ac.uk/10.3390/heritage4040189
Chicago/Turabian StyleIzzo, Francesca Caterina, Arja Källbom, and Austin Nevin. 2021. "Multi-Analytical Assessment of Bodied Drying Oil Varnishes and Their Use as Binders in Armour Paints" Heritage 4, no. 4: 3402-3420. https://0-doi-org.brum.beds.ac.uk/10.3390/heritage4040189