US2317487A - Impregnation of fibrous materials - Google Patents
Impregnation of fibrous materials Download PDFInfo
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- US2317487A US2317487A US380314A US38031441A US2317487A US 2317487 A US2317487 A US 2317487A US 380314 A US380314 A US 380314A US 38031441 A US38031441 A US 38031441A US 2317487 A US2317487 A US 2317487A
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- United States
- Prior art keywords
- oil
- fatty acids
- degrees
- impregnating
- parts
- Prior art date
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- Expired - Lifetime
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- 239000002657 fibrous material Substances 0.000 title description 10
- 238000005470 impregnation Methods 0.000 title description 4
- 235000019198 oils Nutrition 0.000 description 28
- 239000003921 oil Substances 0.000 description 27
- 239000002253 acid Substances 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 239000010425 asbestos Substances 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 229910052895 riebeckite Inorganic materials 0.000 description 9
- 150000005846 sugar alcohols Polymers 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 235000021588 free fatty acids Nutrition 0.000 description 6
- 239000000944 linseed oil Substances 0.000 description 6
- 235000021388 linseed oil Nutrition 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- -1 fish oils Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1025—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by non-chemical features of one or more of its constituents
- C09K3/1028—Fibres
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/47—Oils, fats or waxes natural resins
- C04B41/472—Oils, e.g. linseed oil
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/137—Acids or hydroxy compounds containing cycloaliphatic rings
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/53—Polyethers; Polyesters
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/021—Composition of linings ; Methods of manufacturing containing asbestos
- F16D69/022—Composition of linings ; Methods of manufacturing containing asbestos in the form of fibres
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/02—Inorganic compounds
- C09K2200/0278—Fibres
- C09K2200/0286—Asbestos
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0429—Alcohols, phenols, ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0447—Fats, fatty oils, higher fatty acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0452—Carbohydrates or derivatives thereof
Definitions
- This invention relates to improvements in the art of impregnating fibrous materials.
- the invention is especially applicable for impregnating and hardening of sheets, plates, blocks, etc., such as used in clutches, brakes, etc., when thorough oxydation by air is not possible.
- a typical example for such conditions is a molded brake block compounded from asbestos fiber and other solids with an oil as binder. These brake blocks are cured by exposure to a temperature of 350 to 450 degrees Fahrenheit for many hours. Linseed oil, bodied under vacuum to a high viscosity with very low acidity has been found to be the most suitable material for the purpose, also in combination with phenolic r'esins. I
- the present invention utilizes principally cheap raw materials having a high degree of polymerization and a high acidity, such as still bottoms from the distillation of fatty acids.
- Such materials consist principally of poly merized triglycerides and fatty acids, the latter also mostly polymerized.
- the presence of these free acids prevents the coagulation of the still bottoms at the high temperatures prevailing in the fatty acid stills.
- the fact that the free fatty acids are present in the form of dimers or higher polymers explains the impossibility to distill them off under the vacuum and temperature under which the corresponding monomeric acids distill over.
- drying and semidrying oils can be utilized according to the present invention.
- oils he mentioned linseed oil, perilla oil, China-wood oil, oiticia oil, raw or dehydrated castor oil, walnut oil, poppy seed oil, rapeseed oil, soya bean oil, sunflower oil, fish oils, tall oil, and oils of similar chemical composition.
- oils In utilizing these oils, they are first bodied under heat with or without the addition of fatty acids to a high degree of polymerization and high viscosity. Then a polyhydric alcohol, such as glycerin, sorbitol, pentaerithritol, is added in pressure, without, or preferably with mechanical agitation, under cover of inert gases, such as carbon dioxide or nitrogen, in vessels heated by direct fire, electrically or through a jacket, or in any other manner known to the industry of varnish manufacture, oil bodying or resin manufacture.
- a polyhydric alcohol such as glycerin, sorbitol, pentaerithritol
- a temperature of 400 degrees F. is generally used in the examples cited, a lower temperature is usable particularly when vacuum is applied and. low viscosities are desired. Higher temperatures may be applied especially when less polymerized raw materials are used and when higher viscosities are desired in the finished product.
- Compounds made according to this invention are suitable for many purposes, e. g. impregnation of gaskets, brake lining and clutch facing, asbestos shingles and tile, etc., also as coating material, priming and finishing coat "on asbestos materials, on steel, cast iron and other metals, in the form of sheets, wire, cast or machined parts.
- Particularly waterproof finishes are obtained by incorporation of suitable phenolic resins or com- Example 1 100 parts of still bottoms from the distillation of linseed-oil fatty acids with an acid value of 90 are heated with v parts of glycerin to a temperature of 400 degrees F. under carbon dioxide until the acid value is below 20. Then the product is cooled rapidly.
- the oil thus obtained has a viscosity of 500 poises or more (depending on the degree of polymerization of the raw material), is soluble in hydrocarbon solvents, and when coated on a metal sheet and baked at 350 degrees F. for 2 hours forms a hard, tough film of good elasticity, infusible by heat and sparingly soluble in all organic solvents.
- the product thus obtained is a viscous, brown oil suitable as binder for ,asbestos fibers in the manufacture of brake linings and clutch facing in place of vacuum bodied linseed oil.
- the drying-of the impregnated lining is effected by bakingiat 300 degrees F. or more. Lining of one inch or more thickness is thoroughly cured in the center.
- Example 3 parts of ,p-tertiary-butyl-phenol formaldehyde resin are dissolved by heating to 300 degrees F. in 80 parts of cotton seed pitch. Then 4 parts of glycerin are added and the mass poises at 70 degrees I". Then the acid value is obtained by titration of a sample and after the mass is allowed to cool to 400 degrees F., glycerin is slowly added in an amount of 1.2 times the theoretical amount calculated from the acid value. Heating is continued without reflux until the acid value is below 25.
- a medium light colored oil is obtained of high viscosity, which dries to a very durable film when baked at temperatures above 250 degrees I". and is suitable as coating and impregnating material.
- the resulting product gives a harder drying coating or impregnation of even better water resistance than the products from Examples 1 and 2, and is completely infusible and almost insoluble in any solvent.
- Example 4 20 parts of oiticia oil. parts of linseed pitch, 20 parts of tall oil and 10 parts of phthalic anhydride are heated with 16 parts of sorbitol (85%) to 410 degrees F. with good agitation and after one half hour also under vacuum, until the acid value of the mixture is below 30, then the mass is cooled to 250 degrees F. and 50 parts of toluol are added.
- the resulting varnish is suitable as insulating varnish for wire coating of excellent hardness and flexibility.
- Example 5 80 parts of raw linseed oil are heated while carbon dioxide is passed through the oil with 20 parts of fatty acids. obtained by saponification of dehydrated castor oil to a temperature of 580 degrees F. until the viscosity of a sample is 35 said mixture.
- the process consisting in' polymerizing drying oils in the presence of fatty acids to high viscosity; in partially esterifying the free acids contained in said polymerized drying oils with polyhydric alcohols; .in applying the product resulting from the partial esterification to Y the material to be impregnated and in substantially finishing the esteriflcation of the free acids contained in said polymerized drying oils by subjecting said material to a baking process.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Structural Engineering (AREA)
- Mechanical Engineering (AREA)
- Braking Arrangements (AREA)
Description
Patented Apr. 27, 1943 MPREGNATION OF FIBROUS MATERIALS Erich, Schuelke, deceased, late 01' Saddle River, N. J., by Amielotte Schuelke, 'administratrix,
Saddle River, vN. J.
No Drawing. Application February 24, 1941, Serial No. 380,314
7 Claims.
This invention relates to improvements in the art of impregnating fibrous materials. The invention is especially applicable for impregnating and hardening of sheets, plates, blocks, etc., such as used in clutches, brakes, etc., when thorough oxydation by air is not possible. I
It has always been a problem to impregnate fibrous materials, such as asbestos, with a binder which will withstand exposure to high temperatures, particularly when the fibrous material consists of thick sheets or plates. Impregnation by drying oils, unless especially prepared, does not give satisfactory results under such conditions, as in the case of thick plates the oxygen of the air cannot penetrate into the center of such plates, in order to effect drying by oxydation. Therefore, the center will remain softer than the outside.
. A typical example for such conditions is a molded brake block compounded from asbestos fiber and other solids with an oil as binder. These brake blocks are cured by exposure to a temperature of 350 to 450 degrees Fahrenheit for many hours. Linseed oil, bodied under vacuum to a high viscosity with very low acidity has been found to be the most suitable material for the purpose, also in combination with phenolic r'esins. I
The present invention utilizes principally cheap raw materials having a high degree of polymerization and a high acidity, such as still bottoms from the distillation of fatty acids.
Such materials consist principally of poly merized triglycerides and fatty acids, the latter also mostly polymerized. The presence of these free acids prevents the coagulation of the still bottoms at the high temperatures prevailing in the fatty acid stills. The fact that the free fatty acids are present in the form of dimers or higher polymers explains the impossibility to distill them off under the vacuum and temperature under which the corresponding monomeric acids distill over.
He discovered that such still bottoms, when heated with polyhydric alcohols, e. g. glycerin, in a quantity suificient to esterify the free fatty acids in the still bottoms to a point, where all the alcohol is combined to' form mono or diesters, the resulting material forms an excellent impregnating and. coating base, which upon baking at the usual temperatures of 350 to 450 degrees Fahrenheit solidifies completely due to the completion of esteriflcation, and becomes insoluble and infusible by heat.
He also discovered that such partially esterified still bottoms are excellent solvents for phenolic resins, probably due to the free hydroxyl groups. In cases where greater hardness of the polymerized binder is required, a solution of such resins in the partially esterified compound was found to be very suitable.
Not only still bottoms, but drying and semidrying oils can be utilized according to the present invention. As such oils he mentioned linseed oil, perilla oil, China-wood oil, oiticia oil, raw or dehydrated castor oil, walnut oil, poppy seed oil, rapeseed oil, soya bean oil, sunflower oil, fish oils, tall oil, and oils of similar chemical composition.
In utilizing these oils, they are first bodied under heat with or without the addition of fatty acids to a high degree of polymerization and high viscosity. Then a polyhydric alcohol, such as glycerin, sorbitol, pentaerithritol, is added in pressure, without, or preferably with mechanical agitation, under cover of inert gases, such as carbon dioxide or nitrogen, in vessels heated by direct fire, electrically or through a jacket, or in any other manner known to the industry of varnish manufacture, oil bodying or resin manufacture.
While a temperature of 400 degrees F. is generally used in the examples cited, a lower temperature is usable particularly when vacuum is applied and. low viscosities are desired. Higher temperatures may be applied especially when less polymerized raw materials are used and when higher viscosities are desired in the finished product.
Compounds made according to this invention are suitable for many purposes, e. g. impregnation of gaskets, brake lining and clutch facing, asbestos shingles and tile, etc., also as coating material, priming and finishing coat "on asbestos materials, on steel, cast iron and other metals, in the form of sheets, wire, cast or machined parts. Particularly waterproof finishes are obtained by incorporation of suitable phenolic resins or com- Example 1 100 parts of still bottoms from the distillation of linseed-oil fatty acids with an acid value of 90 are heated with v parts of glycerin to a temperature of 400 degrees F. under carbon dioxide until the acid value is below 20. Then the product is cooled rapidly. The oil thus obtained has a viscosity of 500 poises or more (depending on the degree of polymerization of the raw material), is soluble in hydrocarbon solvents, and when coated on a metal sheet and baked at 350 degrees F. for 2 hours forms a hard, tough film of good elasticity, infusible by heat and sparingly soluble in all organic solvents.
Example 2 100 parts of soya beanioil pitch (still bottoms from the distillation of soya bean fatty acids) with an acid value of 100 are heated with parts of castor oil to a temperature of 450 degrees F. for 1 hour, then for one half hour at 550 degrees F'., then cooled to 400 F., and 5% parts of glycerin are=added and heating at 400 degrees F. continued, until the acid value of the product is below 25.
The product thus obtained is a viscous, brown oil suitable as binder for ,asbestos fibers in the manufacture of brake linings and clutch facing in place of vacuum bodied linseed oil. The drying-of the impregnated lining is effected by bakingiat 300 degrees F. or more. Lining of one inch or more thickness is thoroughly cured in the center.
Example 3 parts of ,p-tertiary-butyl-phenol formaldehyde resin are dissolved by heating to 300 degrees F. in 80 parts of cotton seed pitch. Then 4 parts of glycerin are added and the mass poises at 70 degrees I". Then the acid value is obtained by titration of a sample and after the mass is allowed to cool to 400 degrees F., glycerin is slowly added in an amount of 1.2 times the theoretical amount calculated from the acid value. Heating is continued without reflux until the acid value is below 25.
A medium light colored oil is obtained of high viscosity, which dries to a very durable film when baked at temperatures above 250 degrees I". and is suitable as coating and impregnating material.
What is claimed is:
1. In the art of impregnating of fibrous materials those steps which consist in adding to a mixture of polymerized fatty acids and polymerized fatty acid esters an amount of polyhydric alcohols substantially sufficient to esterify all the free fatty acids contained in said mixture; in esterifying at first only a part of said free fatty acids with said polyhydric alcohols to obtain a viscousoil; in impregnating the fibrous materials to be treated with said viscous oil; in solidifying said oil by subjecting the impregnated materials to a baking process to substantially finish the esterification of the free acids contained in said mixture.
2. In the art of impregnating of fibrous materials those steps which consist 'in adding to a mixture of polymerized fatty acids and polymerized fatty acid esters an amount of polyhydric alcohols substantially sufficient to esterify all the free fatty acidscontained in said mixture; in esterifying at first only a part of said free fatty acids with said polyhydric alcohols to obtain a viscous oil; in dissolving an oil-soluble resin in the raw mixture or in the product resulting from the partial esterification of said mixture; in impregnating the fibrous materials to be treated with said viscous oil; in solidifying said oil by subjecting the impregnated material to a baking process to substantially finish v the esterification of the free acids contained in heated at 400 degrees F. until a sample upon 7 cooling has a viscosity of 500 poises. Then the mass is cooled rapidly to avoid coagulation.
The resulting product gives a harder drying coating or impregnation of even better water resistance than the products from Examples 1 and 2, and is completely infusible and almost insoluble in any solvent.
Example 4 20 parts of oiticia oil. parts of linseed pitch, 20 parts of tall oil and 10 parts of phthalic anhydride are heated with 16 parts of sorbitol (85%) to 410 degrees F. with good agitation and after one half hour also under vacuum, until the acid value of the mixture is below 30, then the mass is cooled to 250 degrees F. and 50 parts of toluol are added.
The resulting varnish is suitable as insulating varnish for wire coating of excellent hardness and flexibility.
Example 5 80 parts of raw linseed oil are heated while carbon dioxide is passed through the oil with 20 parts of fatty acids. obtained by saponification of dehydrated castor oil to a temperature of 580 degrees F. until the viscosity of a sample is 35 said mixture.
3. In the art of impregnating of fibrous ma-' terials, the process consisting in esterifying a part of the free acids contained in still bottoms from the distillation of fatty acids with polyhydric alcohols; in applying the liquid product resulting from the partial esterification to the material to be impregnated and in substantially finishing the esterification of the free acids contained in said still bottoms, by subjecting said material to a baking process.
4. In the manufacture of brake linings and clutch facings the process of thoroughly impregnating and binding together the asbestos fibers of the linings, comprising the heating of still bottoms from the distillation of fatty acids with polyhydric alcohols to partially esterify said still bottoms; impregnating the asbestos fibers of said linings with the viscous oil resulting from said partial esterification of said still bottoms and subjecting the linings, to a baking process.
5. In the manufacture of brake linings and clutch facings the process of thoroughly impregnating and binding together the asbestos fibers of the linings, comprising the heating of still bottoms frorn the distillation of soya bean fatty acids with castor oil and glycerin to partially esterify said soya bean oil pitch; impregnating the asbestos fibers of said linings with the viscous oil. resulting from said partial esterification of the soya bean oil pitch and subjecting the linings, to a baking process.
in the presence of fatty acids obtained by the 6. In the art of impregnating offibrous materials, the process consisting in' polymerizing drying oils in the presence of fatty acids to high viscosity; in partially esterifying the free acids contained in said polymerized drying oils with polyhydric alcohols; .in applying the product resulting from the partial esterification to Y the material to be impregnated and in substantially finishing the esteriflcation of the free acids contained in said polymerized drying oils by subjecting said material to a baking process.
7. The process of impregnating of fibrous materials, consisting in polymerizing raw linseed oil saponiflcation of dehydrated castor oil, in adding an amount 01 glycerine substantially suflicient to esterify all the free fatty acids contained in said polymerized products; in partially esterifying the free acids contained in said polymerized products; in applying the resulting oil to the material to be impregnated and in substantially finishing the esterification by subjecting said ma-- terial to a baking process.
ANNELO'I'I'E SCHUELKE, Administmtria: of the Estate of Erich Schuelke,
deceased.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US380314A US2317487A (en) | 1941-02-24 | 1941-02-24 | Impregnation of fibrous materials |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US380314A US2317487A (en) | 1941-02-24 | 1941-02-24 | Impregnation of fibrous materials |
Publications (1)
Publication Number | Publication Date |
---|---|
US2317487A true US2317487A (en) | 1943-04-27 |
Family
ID=23500703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US380314A Expired - Lifetime US2317487A (en) | 1941-02-24 | 1941-02-24 | Impregnation of fibrous materials |
Country Status (1)
Country | Link |
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US (1) | US2317487A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2465858A (en) * | 1944-10-09 | 1949-03-29 | Johns Manville | Bonded fibrous shape and method of making same |
US2486353A (en) * | 1949-10-25 | Coating compositions comprising re | ||
US2620319A (en) * | 1950-06-08 | 1952-12-02 | Bonafide Mills Inc | Surface covering sheet and method of making the same |
US2684177A (en) * | 1950-07-18 | 1954-07-20 | Gen Electric | Coated baking pan and method of making same |
US2692211A (en) * | 1951-06-07 | 1954-10-19 | Lovell Chemical Company | Process for drying a cyclic pentene impregnated asbestos sheet |
US2791502A (en) * | 1954-12-17 | 1957-05-07 | Congoleum Nairn Inc | Felt product and process therefor |
US2875899A (en) * | 1952-09-25 | 1959-03-03 | Gen Motors Corp | Oil filter coating |
US2956908A (en) * | 1956-04-25 | 1960-10-18 | Brownback Henry Lowe | Oil resistant coated gasket material |
US3056708A (en) * | 1959-05-13 | 1962-10-02 | West Virginia Pulp & Paper Co | Mineral fiber mat formation |
US3096230A (en) * | 1960-06-23 | 1963-07-02 | Southwick W Briggs | Filter medium |
US4489109A (en) * | 1982-12-10 | 1984-12-18 | Asarco Incorporated | Process for applying latex rubber coatings to asbestos-cement products |
-
1941
- 1941-02-24 US US380314A patent/US2317487A/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2486353A (en) * | 1949-10-25 | Coating compositions comprising re | ||
US2465858A (en) * | 1944-10-09 | 1949-03-29 | Johns Manville | Bonded fibrous shape and method of making same |
US2620319A (en) * | 1950-06-08 | 1952-12-02 | Bonafide Mills Inc | Surface covering sheet and method of making the same |
US2684177A (en) * | 1950-07-18 | 1954-07-20 | Gen Electric | Coated baking pan and method of making same |
US2692211A (en) * | 1951-06-07 | 1954-10-19 | Lovell Chemical Company | Process for drying a cyclic pentene impregnated asbestos sheet |
US2875899A (en) * | 1952-09-25 | 1959-03-03 | Gen Motors Corp | Oil filter coating |
US2791502A (en) * | 1954-12-17 | 1957-05-07 | Congoleum Nairn Inc | Felt product and process therefor |
US2956908A (en) * | 1956-04-25 | 1960-10-18 | Brownback Henry Lowe | Oil resistant coated gasket material |
US3056708A (en) * | 1959-05-13 | 1962-10-02 | West Virginia Pulp & Paper Co | Mineral fiber mat formation |
US3096230A (en) * | 1960-06-23 | 1963-07-02 | Southwick W Briggs | Filter medium |
US4489109A (en) * | 1982-12-10 | 1984-12-18 | Asarco Incorporated | Process for applying latex rubber coatings to asbestos-cement products |
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