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Product Information
Table of contents 3 4 6
Introduction
Introduction
The chemical structure of polyglycols is readily understood in terms of the general principle of their synthesis. Applications 36 The various polyglycol types are obtainable by means of anionic polymerization of oxirans using an alcohol or alcoholate as an initiator. As shown in Fig. 1, a wide variety of products for many applications are made beginning with different initiating alcohols 36 36 37 37 37 37 37 38 38 Figure 1 38 38 38 39 39 The different product series are generally identified more spe39 39 40 40 40 40 41 41 41 cifically by a letter code indicating the start molecule or the terminal groups. For example, M refers to methanol, B butanol, A allyl and P pentaerythritol. The numbers that follow indicate the ratio of ethylene oxide to propylene oxide and the molecular weight. ROH + n H2C-CH2 + m H2C-CHCH3 RO(CH2CH2O)n(CH2CHCH3O)mH O O (ROH) by varying both the ratio of the epoxide building blocks (n : m) and the molecular weight (n + m). Essential properties such as water solubility or hydrophilia are determined by the mixing ratio of ethylene oxide and propylene oxide. The viscosity and hydroxyl value of a polyglycol series is influenced by the number of polymerized epoxide building blocks. Reactivity of the various polyglycols with a wide variety of reagents is influenced by the initiating alcohols used and their reactive groups that persist after polyglycol synthesis as well as by the free hydroxyl groups.
36
Technical ceramics / Powder metallurgy Production of rubber and elastomers polyglycols as lubricant and mould release agents and as vulcanization activators Overview of products Plasticizers, modifiers, processing aids in plastic manufacturing Paper industry, wood and cellophane processing Additives in the building materials industry Binding agents for detergent tablets (cleaning agents for clothes, dishes, denture cleaners) Technical data 6 12 14 16 18 20 22 Additives in fibre, textile and leather processing Anticaking treatment / Spray-coating of fertilizers Polyethylene glycols M-type polyglycols A and V-type polyglycols PR-type polyglycols B11-type polyglycols P41-type polyglycols B01 / T01-type polyglycols and enzymes Pharmaceutical and cosmetic preparations Modifiers in viscose production Solvents and additives in paints, inks, coatings and adhesives Reactions with polyglycols Esterifications Reactions with isocyanates Reactions with epoxides Reactions with functionalized polyglycols
24
Solubility
allyl polyglycols Properties 24 24 28 28 31 32 32 Reactions with functionalized polyglycols vinyl polyglycols Components for lubricants Fire resistant hydraulic fluids Gear lubricants for extreme temperatures Lubricants for gas and refrigeration compressor Lubricant greases Quenching bath additives Metalworking/plastics processing
Viscosity / Melting point Hygroscopicity Volatility and thermal stability Molar mass distribution / Hydroxyl value Particle size distribution / Powder density Physiological behaviour / Pharmaceutical and food approvals
42
2
P O LYA L K Y L E N E G LY C O L S / P O LY E T H Y L E N E G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
Overview of products
Polyethylene glycols (PEGs)
Polyethylene glycols are linear homopolymers of ethylene oxide. They are available in a molecular weight range of 200 to 35,000. The physico-chemical properties of polyethylene glycol are essentially determined by the two free hydroxyl groups and the ether oxygen atoms. The available product forms for PEG types 3,000 to 20,000 include flakes (S) and powder (P); types 3,0008,000 are also available as fine powder (PF). Types 1,5008,000 are also supplied to large-volume customers in heated tank lorries in the form of melts (FL).
PR-type polyglycols
The chemical structure of PR-type polyglycols is nearly the same as that of pure polyethylene glycols with the same molar mass. Their chemical properties and applications are comparable accordingly. The essential difference seen in these products is a central branching. Due to this, their melting point / pour point is 20 to 30C lower than that of pure polyethylene glycols with the same molar mass. As with all polyglycols, they show practically no tendency to evaporate, even at temperatures >100C.
P41-type polyglycols
The physico-chemical properties of the polyglycols of the P-41 series are determined by the four free hydroxyl groups and the ethylene oxide : propylene oxide ratio of 4:1. Due to their low comonomeric proportion of propylene oxide groups, P41-type polyglycols have melting points / pour points of 0 to -10C independent of molar mass, are very readily water-soluble and have cloud points at approximately 80 to 90C. At room temperature they are light, highly viscous liquids. P41-type polyglycols are insoluble in pure hydrocarbons. As is the case with the other polyglycols, they show practically no tendency to evaporate, even at >100C.
Special products
Our development department is well-equipped to develop on the basis of a number of initiators and epoxide components special customized products in addition to those shown in the tables on the next pages.
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
CAS-No.: 25322-68-3
Solidification point EP III C approx. -50 approx. -50 -15-10 -15-10 48 48 1722 1722 1722 2530 3540 3540 4448 4448 4852 4852 5256 Viscosity at 20C (50% aqueous solution) mPas 6067 (undiluted) 6067 (undiluted) 8896 (undiluted) 8896 (undiluted) 112124 (undiluted) 110125 (undiluted) 1718 1619 1619 2123 2429 2429 3642 3642 5058 5056 7595 Density at 20C (DIN 51757) g / cm3 1.124 1.124 1.125 1.125 1.126 1.126 1.26 1.26 1.26 1.126 (melt) 1.126 (melt) 1.126 (melt) 1.20 (melt) 1.20 (melt) 1.20 (melt) 1.20 (melt) 1.20 (melt) pH at 5% (DIN 19268) 5.07.0 4.56.0 5.07.0 4.07.0 5.07.0 4.07.0 5.07.0 5.07,2 3.05.0 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 Water content (DIN 51777) % (m / m) max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0,1 max. 0,1 max. 0.5 max. 0.5 max. 0,15 max. 0.5 max. 0,1 max. 0.5 max. 0,1 max. 0.5 Refractive index nD20 (DIN 51423) ( 0.002) 1.460 (20C) 1.460 (20C) 1.464 (20C) 1.464 (20C) 1.467 (20C) 1.467 (20C) 1.452 (70C) 1.452 (70C) 1.452 (70C) 1.452 (70C) 1.453 (70C) 1.453 (70C) 1.454 (70C) 1.454 (70C) 1.454 (70C) 1.454 (70C) 1.455 (70C) Residual EO GC mg / kg max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 Residual Dioxan GC mg / kg max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 max. 1 Maximum solubility in water %m / m at 20C unlimited unlimited unlimited unlimited unlimited unlimited unlimited unlimited unlimited 80 75 75 62 62 58 58 56 Vapour pressure at 20C hPa < 0,1 < 0,1 < 0,1 < 0,1 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 Oxide ash (DIN 51575) %m / m max. 0.05 max. 0.01 max. 0.05 max. 0.01 max. 0.05 max. 0.01 max. 0.05 max. 0.01 max. 0.01 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 PEG-32 PEG-32 PEG-40 PEG-40 PEG-60 PEG-16 PEG-20 PEG-12 PEG-8 PEG-6 INCI designation PEG-4 Application characteristics
200 200 G 300 300 G 400 400 G 600 600 A 600 PU 800 1000 1000WA 1500 S 1500 FL 2000 S 2000 FL 3000 S
Functionality Hydroxyl value (DIN 53240) mg KOH / g Dihydroxy534591 DihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxyDihydroxy534591 356394 356394 267295 267295 178197 178197 178197 134148 107118 107118 7080 7080 5162 5162 3442
Solvent / chemical synthesis Reduced alkali content for synthesis and polyurethane applications Solvent / chemical synthesis Reduced alkali content for synthesis and polyurethane applications Solvent / chemical synthesis Reduced alkali content for synthesis and polyurethane applications Solvent / chemical synthesis Reduced alkali content for synthesis and polyurethane applications Reduced alkali content for synthesis and polyurethane applications Chemical synthesis / aqueous solutions Chemical synthesis / aqueous solutions Reduced alkali content for synthesis and polyurethane applications Humectant / binder / release- / processing agent / synthesis / aqueous solutions Product form with reduced water content for chemical syntheses Humectant / binder / release- / processing agent / synthesis / aqueous solutions Product form with reduced water content for chemical syntheses Humectant / binder / release- / processing agent / synthesis / aqueous solutions
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
Powder 3,7004,400 Melt Fine powder Melt Flakes 3,7004,400 3,7004,400 5,1005,900 5,6006,600
Powder 5,6006,600 Spray powder Melt Fine powder Flakes 5,6006,600 5,6006,600 5,6006,600 7,0009,000
Powder 7,0009,000
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
Powder min 16,000 Flakes Flakes Flakes min 16,000 min 16,000 approx. 35,000
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
11
CAS-No.: 9004-74-4
Viscosity at 50C mm2 / s 911 911 911 1721 1721 2935 2531 (50% in water at 20C) 4555 (50% in water at 20C) 4555 (50% in water at 20C) 150180 (50% in water at 20C) 150180 (50% in water at 20C) Density at 50C (DIN 51757) g / cm3 1.090 1.090 1.090 1.074 1.074 1.083 pH at 5% (DIN 19268) 6.08.0 5.07.0 3.05.0 5.07.0 3.05.0 5.07.0 5.07.0 Water content (DIN 51777) % (m / m) max. 0.2 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.3 Refractive index nD at 20C (DIN 51423) ( 0.002) 1.454 1.457 1.457 1.461 1.461 Maximum solubility in water %m / m at 20C unlimited unlimited unlimited unlimited unlimited unlimited approx. 70 Vapour pressure at 20C hPa < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 Oxide ash (DIN 51575) %m / m max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 Methoxy PEG-16 Methoxy PEG-10 INCI designation Application characteristics
MonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxyMonohydroxyMonomethoxy-
Solvent / chemical synthesis / esterification / polyurethane hydrophilization Solvent / chemical synthesis /esterification / polyurethane hydrophilization Reduced alkali content for synthesis and polyurethane applications Solvent / chemical synthesis /esterification / polyurethane hydrophilization Reduced alkali content for synthesis and polyurethane applications Chemical synthesis / esterification / polyurethane hydrophilization Chemical synthesis / esterification / polyurethane hydrophilization Chemical synthesis / esterification / polyurethane hydrophilization Chemical synthesis / esterification / polyurethane hydrophilization Chemical synthesis / esterification / polyurethane hydrophilization Chemical synthesis / esterification / polyurethane hydrophilization
M 2000 S
1,8002,200
25.531
approx. 50
5.07.0
max. 0.5
approx. 50
< 0.01
max. 0.05
M 2000 FL
Melt
1,8002,200
25.531
approx. 50
5.07.0
max. 0.5
approx.50
< 0.01
max. 0.05
M 5000 S
Flakes
4,5005,500
10.212.5
approx. 57
5.07.0
max. 0.5
approx. 50
< 0.01
max. 0.05
M 5000 FL
Melt
4,5005,500
10.212.5
approx. 57
5.07.0
max. 0.5
approx. 50
< 0.01
max. 0.05
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
13
CAS-No.: 126682-74-4
Viscosity at 20C (DIN 51562) mm2 / s approx. 28 approx. 58 approx. 62 / 50C 8496 200300 approx. 100 / 50C approx. 80 2531 (50% in water at 20C) 5057 (50% in water at 20C) 160210 (50% in water at 20C) Density at 50C (DIN 51757) g / cm3 1.069 / 20C 1.089 / 20C 1.084 1.024 1.08 / 20C pH at 10% (DIN 19268) 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 5.07.0 10.012.0 10.012.0 Water content (DIN 51777) % (m / m) max. 0.3 max. 0.2 max. 0.2 max. 0.2 max. 0.3 max. 0.2 max. 0.3 max. 0.3 Refractive index nD at 20C (DIN 51423) ( 0.002) 1.461 1.465 Vapour pressure at 20C hPa < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 Oxide ash (DIN 51575) %m / m max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 Application characteristics
Liquid Liquid Wax / melt Liquid Liquid Liquid Liquid Wax / melt
MonohydroxyMonoallylMonohydroxyMonoallylMonohydroxyMonoallylMonohydroxyMonoallylMonohydroxyMonoallylMonohydroxyMonoallylMonohydroxyMonovinylMonohydroxyMonovinyl-
Iodine Solidivalue fication g / iodine / 100g point EP III C 7585 approx. -12 4853 2227 2833 1518 1215 Not determinable Not determinable approx. +6 approx. +35 approx. -15 approx. -20 approx. -46 approx. +5 approx. 40
Chemical synthesis / hydrosilylation / hydrophilization / reduced alkali content Chemical synthesis / hydrosilylation / hydrophilization / reduced alkali content Chemical synthesis / hydrosilylation / hydrophilization / reduced alkali content Chemical synthesis / hydrosilylation / hydrophilization / reduced alkali content Chemical synthesis / hydrosilylation / hydrophilization / reduced alkali content Chemical synthesis / hydrosilylation / hydrophilization Copolymerization / hydrophilization / emulsification Copolymerization / hydrophilization / emulsification
V 2000
Wax / melt
approx. 2000
MonohydroxyMonovinyl-
2630
Not determinable
approx. 50
10.012.0
max. 0.3
< 0.01
max. 0.05
V 5000
Wax / melt
approx. 5500
MonohydroxyMonovinyl-
8.610.2
Not determinable
approx. 57
10.012.0
max. 0.3
< 0.01
max. 0.05
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
15
CAS-No.: 9003-11-6
Viscosity at 50C (DIN 51562) mm2 / s 1822 2632 3442 5971 5971 Density at 20C (DIN 51757) g / cm3 1.100 1.110 1.115 1.120 1.120 pH at 10% (DIN 19268) 4.07.0 4.07.0 4.07.0 4.07.0 3.05.0 Water content (DIN 51777) % (m / m) max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 Refractive index nD at 20C (DIN 51423) ( 0.002) 1.461 1.465 1.468 1.468 1.468 Vapour pressure at 20C hPa < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 Oxide ash (DIN 51575) %m / m max. 0.01 max. 0.01 max. 0.01 max. 0.01 max. 0.01 INCI designation Application characteristics
DihydroxyDihydroxyDihydroxy-
PR 1000 PU Liquid
Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Reduced alkali content for synthesis and polyurethane applications Lubricant
VP 1962
Liquid
approx. 700
Dihydroxy-
approx. 80
approx. -17
95115
1.124 1.130
8.010.0
max. 0.5
1.494
< 0.01
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
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P O LYA L K Y L E N E
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P O LY E T H Y L E N E
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CH3CH2CH2CH2(OCH2CH2)n(OCH2CHCH3)mOH
Water content (DIN 51777) % (m / m) max. 0.5 max. 0.5 max. 0,15 max. 0.5 max. 0.5 max. 0.5 max. 0.5 max. 0.5 Refractive index nD at 20C (DIN 51423) ( 0.002) 1.457 1.457 1.458 1.459 1.459 1.459 1.460 1.460 Cloud point, 1% in water C approx. 58 approx. 50 approx. 50 approx. 48 approx. 48 approx. 48 approx. 48 approx. 48 Vapour pressure at 20C hPa < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01
CAS-No.: 9038-95-3
INCI designation Application characteristics
B11 / 50 B11 / 70 B11 / 100 B 11 / 150 B11 / 150 K B11 / 300 B11 / 700 B11 / 700 K
MonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxy-
Oxide ash (DIN 51575) %m / m max. 0.01 max. 0.01 max. 0.01 max. 0.01 max. 0.01 max. 0.01 max. 0.01 max. 0.01
PPG-15-Buteth-20
PPG-28-Buteth-35
Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent Solvent / lubricant / chemical synthesis / esterification / defoaming agent
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
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P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
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CAS-No.: 58205-99-5
Oxide ash (DIN 51575) %m / m max. 0.05 max. 0.05 max. 0.05 max. 0.05 max. 0.05 Application characteristics
P41 / 200 P41 / 300 P41 / 3000 P41 / 12000 P41 / 12000 M 80 Genolub 1674
TetrahydroxyTetrahydroxyTetrahydroxyTetrahydroxyTetrahydroxy-
Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Lubricant / thickener / quenching oil
Liquid
Mixture
Mixture
approx. -10
185235
1.090
9.011.0
4.06.0
1.463
> 90C
max. 0.05
20
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
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MonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonobutoxyMonohydroxyMonoisotridecyloxyMonobutoxyPolyhydroxy
PPG-14 Butyl Ether PPG-18 Butyl Ether PPG-24 Butyl Ether PPG-33 Butyl Ether PPG-40 Butyl Ether
Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent Solvent / lubricant / chemical synthesis esterification / defoaming agent
VP 1856 / 1000
Liquid
> 3500
approx. -22
9001100
1.008
5.07.0
max. 0.20
1.453
< 0.01
22
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
23
Physico-chemical properties
cible with water in any ratio, whereby the addition of water lo-
wers the solidification point compared to pure liquid PEG. Solubility in water drops somewhat with increasing molar mass, but never falls below 50% even in PEG 35,000. Dissolution can be accelerated to a considerable degree by heating the substance to above the melting point. The behaviour of PEGs is not ionogenic in aqueous solutions. They are not sensitive to electrolytes and can therefore also tolerate hard water. The water solubility of polyalkylene glycols decreases with the proportion of propylene oxide in the copolymer. This is reflected in a lowering of the cloud point in water. Pure polypropylene glycols such as the B01-type polyglycols are practically insoluble in water. When our PEGs are shipped, the water content is max. 0.5%. Drying down to 0.1% is feasible if necessary by drying at temperatures of up to 165C under vacuum. Using fresh or correctly regenerated molecular sieves (pore size 34 ), the water con-
Figure 2: Viscosity of PEG 20035,000 as a function of temperature mm2 / s 1,000,000 300,000 100,000 30,000 10,000 3,000 1,500
20,00 35 00
50,000 20,000
0
5,000
12,0 10,0
00 00 0 0
2,000 1,000
500
8,00 6,00
300 150
Solubility / Hygroscopicity
The combination of hygroscopic, viscous, lubricating, releasing and binder properties in PEGs with their excellent solubility in water creates ideal conditions for their use in numerous fields of application. The low-molecular liquid PEGs 200600 are mis-
tent can be reduced to 0.05%. Polyglycols are hygroscopic. Their hygroscopicity increases with molecular weight and the proportion of propylene oxide in the comonomer (see Fig. 4). Polyethylene glycols are also readily soluble in many polar organic solvents, for example acetone and methanol. Polyethylene glycols are insoluble in pure hydrocarbons.
200
4,0
100
00 50 00
3,3 3,0
50 30
2,0 15
00
40 25
20 14 10
00 1,3 50
1,0 00 0
PEG
Proportion of propylene oxide 20
80
12 9 7
8 6
60
40
30
0
0
20
Proportion of propylene oxide 100 3 -50 -40 -30 -20 -10 0 10 20 30 40 50 60 10 0 + 20 40 60 80 100
3 120 C
24
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P O LY E T H Y L E N E
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P O LYA L K Y L E N E
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P O LY E T H Y L E N E
G LY C O L S
25
Physico-chemical properties
Figure 4a: Sorption isotherms (23 1C) for PEG 2004,000, glycerol and sorbitol max. water uptake % (m / m) 100 90 80 70 60 50 40 30 Figure 4b: Sorption isotherms for various polyglycols at 23 1C max. water uptake % (m/m) 100 90 80 70 60 50 40
30
20
20
PR 300
er
Gl
20
PE
G1
yc
000
ol
PE
10 9 8 7
10 9 8 7 6 5
M 500
PE
PE
tol
60
40
So
rbi
6
500 G1
5 4
G2 000
P 41 4
PE
PE
B 11
G4
000
2 2
PE
26
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
P O LYA L K Y L E N E
G LY C O L S
P O LY E T H Y L E N E
G LY C O L S
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Physico-chemical properties
Volatility and heat resistance
Polyglycols are not volatile, which is a considerable advantage in view of their applications as plasticizers and humectants. When they are heated to temperatures exceeding 150C, the resulting weight losses are not due to evaporation, but rather to release of volatile decomposition products. Thermal decomposition of polyglycols results neither in hard encrustations nor to deposit of viscous sludge. The decomposition products of polyglycols vary according to air exposure. In addition to water, carbon dioxide and aldehydes, simple alcohols, acids and glycol esters also form. When handling polyglycols at temperatures above 100C, we recommend the addition of suitable oxidation stabilizers. The type and amount of stabilizer required depend on what is expected from the PEG. The following substances have proved useful as antioxidants: 1. Polymeric trimethyldihydroquinoline 2. Diphenylamine derivative 3. Phenothiazine 4. Phenyl-alpha naphthylamine 5. 4,4' methylene-bis-2,6-di-tert-butylphenol 6. Butylated hydroxyanisole 7. Methoxyphenol (hydroxyanisole) On the other hand, purely thermal decomposition without oxygen can hardly be influenced by additives.
Figures indicate % (m/m) = miscible in any ratio cold ss = sparingly soluble at room temperature, soluble at 7080C ins. = insoluble Acetanilide 16% Acetic anhydride Acetone Acrylonitrile Acrylic acid Adipic acid diisopropyl ester Allyl alcohol Ammonia, 25% Amyl acetate Amyl alcohol Aniline Antipyrine 10% Azulene (guajol azulene) 10% Beeswax Benzaldehyde Benzene Benzine Benzocaine Benzoic acid Benzyl alcohol Borax, crystalline Bromo acid Bromobenzene Butanol Butyl acetate Butyl amine Butyl diglycol Butyl glycol ins. ins. 50% 10% 0.3% 10% o-Cresol Copper(II) chloride 2H2O Cyclohexane Cyclohexanol Cyclohexanone *50% ins.
Iodine Iron(III) chloride 6H2O Isobutyl acetate Isobutyl alcohol Isodecyl alcohol Isooctyl alcohol Isopropyl alcohol Isotridecyl alcohol Lactic acid, 90% Lead acetate Lead stearate Lecithin Lithium stearate
Propan-1-ol 1,2-Propylene glycol Pyridine Resorcinol Saccharin Salicylaldehyde Salicylic acid Sorbic acid Sorbitol Sodium chloride Sodium cyclamate Sodium nitrite Sodium sulphate Stearic acid Stearylamine Styrene Styrene oxide Sulphanilamide Sulphathiazole Sulphuric acid, 50%
50% 10% 30% 5% cold ss 0.3% 3% 0.4% ins. cold ss ins. 10% 10%
Solubility of various substances in Polyglykol P41/300, B11/150, M500, PR 600 and T01/35 at 20C / mixing ratio 1:1.
P41/300 B11/150 M 500 PR 600 B01/120 T01/35 Acetic acid Acetone Allyl alcohol Ammonia, 25% Amyl alcohol Aniline Avocado oil Benzaldehyde Benzine Benzene Benzyl alcohol Butanol Butanone Butyl acetate Castor oil Carbon disulphide Carbon tetrachloride Chlorobenzene Chloroform Chlorinated paraffin o-Cresol Cyclohexane Cyclohexanol + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + 10% + + + + + + + + + + + 10% + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + +
Diacetone alcohol Dibutyl phthalate b,b'-Dichloroethyl ether Diethanolamine Diethylene glycol Diethylene glycol dimethyl ether Dimethyl acetamide Dimethyl formamide Dimethyl phthalate Dimethyl sulphoxide Dioctyl phthalate ins. Dioxan Diphenyl ether Di-(2-ethylhexyl)-phthalate ins. Dipropylene glycol Dodecan-1-ol Ephedrine (1/2 H2O) Ester waxes Ethanol Ethyl acetate Ethyl aminoformate Ethyl benzene Ethyl diglycol Ethyl glycol Ethyl glycol acetate 2-Ethyl hexanol Ethylene chloride Formamide Furfural Gelatine Glacial acetic acid Glycerol Glycerol monostearate Glycerol triacetate Glycol Glycolic acid butyl ester Gum Arabic Hexachlorophene Hexadecan-1-ol Hydrochloric acid, 37% 20% ins. 50% ins. cold ss ins. 45% cold ss
Magnesium chloride 4H2O *25% Manganese(II) chloride 4H2O *40% Menthol 10% Mercury(II) acetate *10% Methanol Methoxybutyl acetate Methyl acetate Methyl diglycol Methyl ethyl ketone Methyl glycol Methyl glycol acetate Methyl methacrylate Methyl salicylate Methylene chloride Mineral oils ins. Morpholine -Naphthol Naphthalene Nitrobenzene Nitromethane Octan-1-ol Oil of eucalyptus Oil of lavender Oleic acid Paraffinic oil Paraldehyde PEG-lauric acid ester PEG-sorbitanoleate Perchloroethylene Phenacetin Phenol Phenol, 90% Phenothiazine Phenyl acetate Phenylmercuric acetate Phenyl salicylate Phosphoric acid, 85% Piperazine Polyethylene glycol 4,000 (warm soluble) Polypropylene glycol 400 Potassium iodide 40% 10% 105 10% ins. 50% cold ss 43% 10% 50% 15% 10% 50% 10% ins. *15%
Tannic acid 50% Terpineol Tetrahydrofuran Tetralin 55% Thiourea 10% Thymol 50% Tin(II) chloride 2H2O *55% 1,1,1-Trichloroethane Trichloroethene Trichloro-tert-butyl alcohol 10% Triethanolamine Triethylene glycol tris-(2-chloroethyl) phosphate Urea Vanillin Vaseline Vegetable oils Xylenol Xylene Zinc chloride 2H2O 3% 10% ins. ins. *20%
Calcium chloride 2H2O 20% Camphor 10% Canauba wax ins. Carbon disulphide 10% Carbon tetrachloride Casein ins. Castor oil 1% Catechol 50% Ceresin ins. Cetyl stearyl alcohol cold ss Chloral hydrate 50% Chloramine T 10% Chlorinated paraffin 56 and 70 Chlorobenzene Chloroform Chlorothymol 50% Citric acid 25% Cobalt(II) chloride 6H2O *50% Coconut oil amine 10% Colophony 50%
* These metallic salts become solute when heated to about 100C and form highly viscous liquids with PEG 400 that are also stable at room temperature.
Diethylene glycol + +
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Physico-chemical properties
P41/300 B11/150 M 500 PR 600 B01/120 T01/35 Dimethyl formamide Dimethyl sulphoxide 1,4-Dioxan Dipropylene glycol Ethanol Ethyl acetate Ethyl benzene Ethyl diglycol Ethyl glycol 2-Ethyl hexanol Fluorotrichloromethane Glycerol Glycol Hexane Hexan-1-ol Hydrochloric acid, conc. Kerosene Lactic acid, 80% Linseed oil Methanol Methyl diglycol Methylene chloride Methyl glycol Mineral oil Morpholine + + + + + + + + + + + + + + +hot + + + + + + + + + + + + + + + 30% + + + + 30% + + + + + + + + + + + + + + + + + + Isopropyl alcohol + + + + + +hot + + + + +hot + + + + +hot + + +hot + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + + Nitrobenzene Nitromethane Octan-1-ol Olive oil Oleic acid Paraffinic oil Peanut oil Perchloroethylene Petroleum ether Polyethylene glycol 400 Polyethylene glycol 4,000 Polypropylene glycol 2,000 Spindle oil Stearic acid Sulphuric acid 50% Tetrahydrofuran Tetralin Toluene Trichloroethene Trichloroethyl phosphate Triethanolamine Trixylenyl phosphate Turkey red oil Water Xylene + + + + + + + + + + + + + + + + + + + + + + n = 101 M = 4462 2 n = 51 M = 2262 6 + + + + + + + + n = 21 M = 942 8 + + + + + + + + + + + + + + + + + + + + + + + + + + + + 10 + hot + + +hot + + + + +hot + + + Figure 5: Molar mass distribution of PEG 4004,000 Poisson distribution % (m / m) Propylene glycol + +hot + + + + The molar mass distribution can be calculated by means of gel permeation chromatography (GPC). This distribution range is generally quite narrow for polyethylene glycols (Fig. 5). + + 40% 40% + + + + Molar mass = 56,110 x number of free OH groups per molecule OH value P41/300 B11/150 M 500 PR 600 B01/120 T01/35 + + + + + + + + + + + + + + + + + + + + + +hot + + + + + + + + The various polyglycol types are not chemical compounds with a precisely defined molar mass, but rather polymers with a certain molar mass distribution. Normally, the molar masses Mn calculated on the basis of the hydroxyl value (OH value) are the values listed. A knowledge of the OH value is decisive for many chemical processes involving polyglycols.
Ethylene chloride +
Hexadecan-1-ol +hot
n=9 M = 414
14
12
80
100
120
140 = n
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Physico-chemical properties
Particle size distribution / Powder density
Polyethylene glycols with molar masses of 1,500 to 35,000 are usually supplied in flake form (S types) with flake sizes of 0.52 cm. Powdered (P types) are also available with molar masses of 3,000 to 20,000 as well as fine powders (PF types) at 3,000 to 8,000. Polyethylene glycols in powder form are used where thorough mixing with other types of components in the dry state is important, e.g. in tablet manufacture or preparation of ceramic pressing masses. Table 1 shows the sieve analysis for a typical particle size distribution and the powder density of our polyglycol powders.
Table 1 Particle size distribution of PEG powder Microns Powder 3,00020,000 % < 90 90200 > 200 1020 2035 5570 Fine powder 3,0008,000 % 7590 1020 15
met by the polyglycols. In addition to pharmaceutical listings, approvals of polyglycols for food-related applications are decisive for a large number of applications, mainly in the field of packaging. Both in Germany and the US, polyglycols are listed in the BgVV (German Federal Institute of Consumer Health Protection and Veterinary Medicine) Recommendations and the FDA Code of Federal Regulations for many applications involving potential food contact (Tabs. 2, 3, 4).
Powder density (kg / m3) Flakes 400500 Powder 500700 Fine powder 450550
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Physico-chemical properties
BGVV (German Federal Health Office) Recommendations for PEGs
Table 3
BGVV Recommendation III V VI Class of substance polyethylene polystyrene styrene co- and graft polymers, mixtures of polystyrene with polymers dyestuffs for the coloration of plastics and other polymers polyamides unsaturated polyester resins cellulose film polymer dispersions polyterephthalic acid diole ester natural and synthetic rubber plasticized PVC for conveyor belts crosslinked polyurethane copolymers from ethylene, propylene, butylene, vinyl esters and saturated aliphatic acids, salts and esters paper, board, cartons polyurethanes for paper coating artificial sausage skins (cellulose film) Position as of 01.12.1995 01.12.1995 01.12.1995 End use and limits lubricant, antiblocking agent, antistatic agent, max. 0.25 % antistatic agent, max. 3 % lubricant, mould release agent, max. 8 %* auxiliary, max. 0.35 %** carrier, adhesion promoter, max. 0.2 % mould release agent, lubricant humectant max. 15 % (also triethylene glycol) defoamer, max. 10 % starting substance, max. 0.1 % processing aid, lubricant, mould release agent antistatic agent educt processing aid in uncrosslinked peroxidically crosslinked and ionically crosslinked material, max. 0.1 % humectant raw material polyethylene glycol max. 27.5 %* in conjunction with coating, complying BGVV lubricant, max. 1 %* wax dispersion lubricant, antistatic agent, max. 0.25 % film-former max. 0.2 % monoetyhlene glycol max. 0.2 % monoetyhlene glycol max. 0.2 % monoethylene glycol molar mass at least 400 molar mass at least 1000 max. 0.2 % monoethylene glycol Purity requirements max. 0.2 % monoethylene glycol max. 0.2 % monoethylene glycol max. 0.2 % monoethylene glycol max. 0.1 % monoethylene glycol
01.06.1994 01.12.1995 01.07.1984 25.08.1985 replaced 1989 01.12.1995 01.12.1995 01.12.1995 01.03.1989 01.06.1981 01.12.1995
crosslinked polyethylene materials for the coating of hollow glassware polyethylene hair sprays
max. 0.2 % monoetyhlene glycol max. 0.2 % monoetyhlene glycol max. 0.2 % monoetyhlene glycol max. 0.2 % monoetyhlene glycol
Total quantity of all the auxiliaries used for this purpose Based on colored part of the consumer article
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Applications
thermoplasts. To prevent migration of the polyethylene glycols
Production of rubber and elastomers polyglycols as lubricant and mould release agents and as vulcanization activators
Polyethylene glycols have been used for some time in the rubber and tyre industry. In most cases, PEG 4,000, 6,000 or 8,000 are used. Using the high-molecular PEG 20,000 usually enhances the effect even further. PEGs in the form of a 15% aqueous solution can be sprayed into the vulcanization moulds or added directly to the rubber formula. Polyglycols make mould release easy. They give the vulcanisates an attractive finish which in the case of black goods is distinguished by a deep shade and velvety sheen. In general, foam rubber articles require higher concentrations. By contrast with mineral oils, polyglycols do not attack rubber and can readily be washed off with water. According to the FDA Recommendation for Rubber Articles (21 CFR 177.2600), PEGs have been approved as processing aids, lubricants and release agents for rubber articles that come into contact with food products. As vulcanization activators, for example with highly dispersed silicic acid, the addition of PEGs (especially PEG 6,000 to 20,000) to the vulcanization masses enhances filler dispersion during the mixing process and improves tensile strength modulus and tear resistance of the end product. PEG 1,500 can be used as a processing additive for latex production. The PEG acts as a release agents to prevent sticking.
out of the plastics, use of high-molecular types such as Polyglykol 20,000, 20,000SRU or 35,000 is recommended.
Binding agents for detergent tablets (cleaning agents for clothes, dishes, denture cleaners)
Polyethylene glycols are used as water-soluble binding agents for production and pressing of detergent tablets. The rate of tablet dissolution can be set as desired by selecting the right type and dosage of PEGs.
Antistatic effect No discoloration of fibres due to the influences of light and heat Pure, high-molecular polyethylene glycols are used as formula additives for surface treatment of glass fibres.
crease the flow qualities of liquid fillers and levelling masses. For these applications, dry mixtures of polyethylene glycol powders are added to cement and mortar formulae. Copolymers with M and V polyglycol side branch groups serve to slow down the setting process; they are also used to plasticize and improve the flow characteristics for concrete processing.
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Applications
Esterification products of polyglycols (PEGs, M-PEGs, B11 and In the production of polyesters and polyamides, polyethylene glycols are used to modify the polymeric properties. are highly viscous, water-soluble polyethylene glycols or insoluble gels capable of swelling.
B01 types) as well as additive compounds of silicones and allyl polyglycols are also used as foam regulators and defoaming agents in coatings and paints (see section: Reactions with polyglycols).
shown in Fig. 6. Use of diisocyanates together with dihydrofunctional polyglycols results in linear polyurethanes, whereas use of trifunctional and tetrafunctional isocyanates and polyglycols e.g. polyglycols from the P41 series results in cross-linked polyurethanes. M-type polyglycols contain only one terminal OH group, resulting in chain terminations in reactions with isocyanates. Polypropylene glycols are used most frequently in production of standard polyurethanes. The much more hydrophilic polyethylene glycols are used to modify elasticity, synthesize polyurethane-based thickeners for paints and coatings (as-
Esterifications
Polyglycols can form esters with their free hydroxyl groups. Monoesters, diesters and polyesters can be synthesized depending on the specific functionality of a polyglycol and the acid used. Polyglycols are used as hydrophilic components, for example in the synthesis of stearic or oleic acid esters. The hydrophilic-lipophilic balance (HLB) can be specifically controlled by selecting an appropriate polyglycol. Polypropylene glycols and ethylene oxide / propylene oxide copolymers such as the products from the B01, B11 or MP series have secondary hy-
sociative thickeners) and in production of aqueous polyurethane dispersions. Decisive factors in reactions with isocyanates are the purity and low water content of the polyglycols used. Clariant carries a number of special polyglycols for these applications. Figure 6: Reaction of polyglycols with isocyanates O O HO-(CH2CH2 O)nH + 2R-N=C=O R-NH-C-O(CH2CH2O)n-C-NH-R Polyglycol Isocyanate Polyurethane
droxyl groups in contrast to pure ethylene oxide polymers. These groups are more difficult to esterify, although the resulting esters are then more stable against hydrolysis. Esterification of monohydro-functional polyglycols of the M and B series with methylacrylic acid, maleic acid or other unsaturated acids results in macromonomers capable of radical copolymerization. Their hydrophilic properties exert an essential influence on the solubility and dispersion characteristics of the resulting polymers. Use of dihydrofunctional PEGs in the same esterification process results in water-soluble cross-linking agents for radical polymerizations. Reactions of the free hydroxyl groups in polyglycols with epoxides, such as for example glycidyl methacrylate, can be used to provide various reactive groups available for further reactions with the hydrophilic polyglycol chain. Dihydroxyfunctional polyethylene glycols can be cross-linked to diepoxides such as bisphenol-A-diepoxide. Depending on the proportion of diepoxide and on the polyglycol used, the results
bilizers in emulsion and suspension polymerization. With their single free OH group, V-type polyglycols can also be used in a wide variety of chemical reactions. In reactions with isocyanates and/or polyesters, a reactive vinyl group is integrated in the resulting polymer. Hydrophilysation of silicones is obtained by additive hydrosilation of both Vand allyl polyglycols. As is the case with all vinyl ethers, V-type polyglycols tend to break down the vinyl function in an acidic environment.
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Applications
Polyglycols of the PR series can be used for the formulation of compressors that are used for the polymerisation of ethylene or propylene. The solubility of ethylene in B11/150K polyglycol under comparable pressure conditions is only one tenth of the solubility in Gear lubricants for extreme temperatures Polyglycols are characterised by a shallow viscosity-temperature curve (high VIE -Index), insensitiveness to shearing, outstanding wear protection, excellent ageing stability as well as low friction values and very low solidification points. Consequently polyglycols, but particularly those of the B01, B11 and T01 series, are ideally suited for the formulation of synthetic hydraulic fluids and the lubrication of enclosed, high-load industrial transmission gears, e.g. in rolling mills, feed mills, kneaders and conveyors. As a result of their low coefficient of friction the use of polyglycols as a lubricant in wormgear transmissions, the oil temperature can be reduced and the lubrication efficiency increased, Fire resistant hydraulic fluids (HFC) Fire resistant hydraulic fluids are used extensively for safety reasons in many industries (mining, foundries, aluminium and die-casting industry). The composition of these fluids is as follows: Approx. 45 % water as the non-combustible constituent Approx. 25 % ethylene-, diethylene-, triethylene- or propyleneglycol as anti-freeze compound Approx. 20 % highly viscous, water-soluble polyglycol (e. g. Polyglycol P41/12000) to achieve the required viscosity and lubricity Approx. 10 % additives to avoid liquid- and gaseous-phase corrosion, as anti-foaming agent and wear protection. The polyglycol/additive mixing ratio is of decisive importance for the quality of the formulation. Water-glycol hydraulic fluids have a clearly more favourable ecological profile than mineral oil or fully synthetic formulations. Lubricants for gas and refrigeration compressors Conventional, mineral oil based lubricants tend to absorb nonpolar gases while oxidation increases their viscosity. Polyglycols, on the other hand, absorb far less gases such as methane, ethane, ethylene or propylene on account of their polar character. This makes polyglycols, but particularly those of the B11 series, ideal lubricants for gas compressors. Consequently the B11/700K and B11/150K types are ideal polyglycol lubricants for Quenching bath additives The polyglycols P41/3000 and P41/12000 have proved their worth as an additive for quenching baths. The formation of a water vapour skin during the quenching process is avoided, and with it soft spots and cracking. The maximum cooling rate is diminished in a targeted manner and shifted towards higher temperature. The amount added to quenching baths is in the order of 2 5 % polyglycol. In correspondingly designed vehicles polyglycols can be used to lubricate the rear axle transmission. The Lubricant Additive 1655 is ideal for the formulation of polyglycol gear transmission oils. For instance 1 part of Lubricant Additive 1655 and 15 parts polyglycol B01/120 results in an outstanding ageing resistance and a breakdown load stage exceeding 12 in the tightened FZG test conditions (A/16.6/90). Lubricant greases High-quality lubricant greases, particularly for use involving high and very low temperatures, can be produced with polyglycols. Modified bentonite or pyrogenic silicic acid can be used as thickeners. Hydrocarbon resistant greases can be produced with water-soluble polyglycols, e. g. the B11 or PR types. thereby significantly extending the service life of the given machine. Low-viscous polyglycols of the B11 and B01 series containing the corresponding additives are also used to lubricate refrigeration compressors in conjunction with different refrigerants (e.g. R134 A.) High load bearing capacity also without additives Favourable viscosity-temperature behaviour The viscosity is less dependent on the pressure The danger of catalyst poisoning is minimised because polyglycols do not contain any sulphur The compressed gas can be readily removed by washing with More detailed examples for the use of polyglycols as lubricants are given below: water white oil. In addition to lower solubility of the gases that are being compressed, lubricant consumption is much lower than with white oil. Other advantages of polyglycols for use as compressor lubricants include: Water-soluble polyglycols of the P41, PR and B11 series are ideal heating conducting fluids for use in tempering plastic parts, for pressureless vulcanisation and for the production of PC-boards in the electrical industry. In all instances the polyglycol based heat carrier/lubricating medium can be easily washed off with water. Metalworking/plastics processing Polyglycols, e. g. polyglycols of the PR and P41 series, are suitable for the formulation of water-soluble, fully synthetic cooling/cutting lubricants and spark erosion fluids and for machining steel, castings and lead-free alloys. A typical formulation would consist of 1050 % Polyglycol P41/3000 and 5090 % Hostacor IT. 15 % solutions are used, depending upon the complexity of the machining process.
biologically degradable hydraulic fluids that are ecologically and toxicologically harmless. These hydraulic fluids are extensively used in the food processing industry.
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Notes
Our products are constantly upgraded on the basis of the latest research results. Products may occasionally be deleted in the course of updating the sales range. Development products that have reached the production stage are not included in this list. This information is based on our present knowledge and is intended to provide general notes on our products and their uses. It should not therefore be construed as guaranteeing specific properties of the products described or their suitability for a particular application. Any existing industrial property rights must be observed. The quality of our products is guaranteed under our General Conditions of Sale. September 2002
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