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  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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  • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
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  • D06M13/402—Amides imides, sulfamic acids
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  • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/59—Polyamides; Polyimides
  • D06M15/592—Polyamides; Polyimides made from polymerised unsaturated fatty acids and polyamines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2215/26—Amines
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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  • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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  • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

• the present invention is directed to a reaction product that is a polymeric composition derived from polyamines through chain extension and reaction with fatty acids that are useful as
• surfactants 10 surfactants, emulsifiers, dispersants and lubricants, and particularly fiber lubricants.
• polymeric fat acids which are a mixture of dibasic and tribasic acids with molecular weights of approximately 560 to 840.
• the polymeric fat acids are derived from vegetable oils, such as soybean, linseed and cottonseed oils, and their glycerides contain substantial amounts of
• Some lubricants are useful as fiber lubricants in the manufacture and processing of various natural and synthetic fibers and/or strands such as polyesters, polyacrylics, polyolefins, polyamides and glass. Some of these lubricants that are cationic in
• 25 nature include the reaction of tetraethylenepentamine and stearic acid, and partially amidated polyalkyleneamines that are reaction products of a mixture of C to C- ⁇ g fatty acids with a polyethylenimine having a molecular weight of about 1200. These reaction products have a residual amine value of from about 300 to
• the present invention is a polymeric reaction product of one or more polyorgano amine compounds having alkyl, aryl, and/or alkylaryl groups with a chain extender and with one or more fatty acid materials.
• the polyorgano amine compounds can be reacted simultaneously or sequentially with the chain extender and/or the fatty acid materials.
• the chain extender is difunctional for reaction with the amine groups of the polyamine. The number of carbon atoms for the chain extender and the amount of amine functionality on the polyamine is balanced to produce at least a water-dispersible chain-extended polyamine.
• the one or more fatty acid materials are predominantly monovalent for reaction with the polyorgano amine compound or the chain-extended polyamine ultimately to produce the chain-extended polyamine with at least one fatty acid moiety that is at least water-dispersible.
• This polymeric reaction product has:
• repeating units derived from the at least trifunctional alkylene, arylene, or araalkylene polyamine having a molecular weight up to around 800 and II) repeating units derived from a polyfunctional, which is predominantly difunctional, chain extender (X-R-Y) wherein R is selected from alkylene, and difunctional alkyl radicals having a number of carbon atoms so that when balanced with the quantity of the amine content of the polyamine results in a reaction with the polyamine to produce at least the water-dispersible chain-extended polyamine, and
• Fatty Acid Material fatty acids, fatty acid esters, fatty acid halides or anhydrides of the acid, and mixtures of these with compounds within the same class and between classes hereinafter collectively referred to in the specification and claims as "Fatty Acid Material". These are predominantly monofunctional in reaction with the chain extender and predominantly saturated.
• the saturated Fatty Acid Materials generally have a number of carbon atoms in the range of from greater than 6 and up to around 22 carbon atoms.
• the number of carbon atoms generally is in the range of from 2 to 22 carbon atoms when, used in a mixture with a minor amount of the Fatty Acids Materials having less than around 6 carbon atoms.
• the ratio of these materials forming the reaction product can be for every monomeric unit of II there is from at least around 1 of I and at least around 0.1 of III and can be 4 of II and 10 for III.
• the polyamine useful in forming the polymeric reaction product of the present invention can be any polyamine having three or more amine groups and can have a molecular weight up to around 4,000 but preferably up to around 800.
• Particularly suitable polyamines have the formula of an H2 -(C n H2 n H) ⁇ -H wherein n can range from around 2 to 6 and preferably is around 2 and/or 3 and x can range from around 2 through around 40 and preferably from 2 through 6.
• the polyamine can include a minor amount, generally, if present, in an amount of less than 50 weight percent of the polyamine of diamines such as ethylenediamine and the like. The preparation of these materials is well known in the art and can be prepared by any of the known methods.
• a desired alkylene polyamine results from the reaction of an appropriate alkylene dihalide and ammonia.
• suitable polyalkyleneamines include diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaeth lenehexamine (PEHA), dipropylenetriamine (DPTA), tripropylenetetramine (TPTA), tetrapropylenepentamine (TPPA), pentapropylenehexamine (PPHA), and dihexmethylenetriamine (DHMTA).
• Such mixed polyalkylenepolyamines can be readily prepared, for example, by condensing ethylene diamine with one more proportions of acrylonitrile to form N-cyanoethyl ethylenediamine which can then be reduced, for example, by catalytic hydrogenation, to form a mixed alkylene polyamine.
• the polyamine can be one or more polyalkyleneimines where the alkyl portion of the molecule can have from 2 to about 12 carbon atoms like polyethyleneimine, polypropyleneimine, polybutyleneimine, and the like that can have a molecular weight of around 800 up to around 50,000 or higher.
• These polyalkylenimines can be prepared by any method known to those skilled in the art.
• the polyfunctional but predominantly difunctional organo compounds useful as chain extenders are compounds where the polyfunctional but chiefly difunctional moieties can react with the nitrogen through the active hydrogens of a residual amine of the polyamine to form a covalent bond.
• chain-extender it is meant, in addition to the aforementioned characteristics, that the reaction of the polyfunctional organo compound increases the molecular weight of the polymeric reaction product through predominantly its difunctionality so that the molecular linkages are more spaced apart from each other as opposed to tight-knit crosslinks that can result in gellation.
• the reaction between the chain- extender and the polyamine can occur either at the primary amine groups at the ends of the polyamine backbone or with any primary and/or secondary amines along the backbone.
• reaction predominantly occurs at the ends of the backbone and reaction along the backbone only occurs to a minor extent.
• These predominantly difunctional organo compounds generally are liquid or solids that melt at temperatures less than around 200°C, and generally can be saturated materials. Some of these compounds also may lead to the formation of imidazolines.
• the chain extender is chiefly difunctional in reaction with the polyamine but a minor amount of polyfunctional organo or organic compound can be present that can react difunctionally with the polyamine.
• Particularly suitable chain extending organo compounds include those having the formula (X-R ⁇ -Y) wherein R ⁇ is selected from alkylene, difunctional alkyl and/or aryl radicals having preferably around 2 to around 15 carbon atoms, and where X and Y are each the same or different functional moieties selected from the following moieties: carboxylic acid and/or esters and/or anhydrides, epoxide, also known as glycidyl or oxirane; halides, like acid chlorides; isocyanates so that the compound is at least diepoxide, dihalide, diacid chloride and/or diisocyanate.
• R ⁇ is selected from alkylene, difunctional alkyl and/or aryl radicals having preferably around 2 to around 15 carbon atoms
• X and Y are each the same or different functional moieties selected from the following moieties: carboxylic acid and/or esters and/or anhydrides, epoxide, also known as glycid
• More specific examples include: bisphenol A diglycidylether, butane diol diglycidyl ether, novalac epoxy, diglycidyl ethers, dichloroethanes, dichloropropane and the like.
• the carbon chain length like that of a hydrocarbon chain between the two functional groups should be satisfactory to allow production of at least water dispersible chain-extended polyamine with or without fatty acid moieties and preferably a water-soluble or e ulsifiable chain-extended polyamine with or without fatty acid moieties.
• Suitable examples of one type of chain extender the dicarboxylic acid with a short hydrocarbonyl chain, include: oxalic acid, alonic acid, succinic acid, glutaric acid, adipic acid, and pimelic acid. These materials are from a well known class of acids and their method of preparation is well known to those skilled in the art. Also, halogenated derivatives of the dicarboxylic acids or the anhydrides or esters of the acids can be used as the chain extenders. Additionally, these types of chain-extenders can be used as part of a mixture with fatty acids for condensation reaction with polyamines.
• the difunctional organic chain extenders can be used individually or in a mixture of chain extenders. Although saturated carboxylic acids are preferred, a small amount of unsaturated dicarboxylic acids such as maleic acid and the like can be used in admixture with the saturated dicarboxylic acids. It is most preferred to use an ester form like dialkyl succinate, for instance, diethyl succinate.
• the conditions for reacting the polyamine which term includes polyalkylenepolyamine or the reaction product of the polyamine and the fatty acid material and the difunctional organo chain extender depend to a degree on the particular compounds that are used. Generally, the reaction is that of less than an excess of the chain extender but at conditions to allow for reaction of a substantial portion if not all of the chain extender.
• the temperature can be about 80°C to about 180°C, while with a diepoxy compound lower temperatures even at or around room temperature can be used while the diacid chain extenders can have a high temperature around 180°C to around 220°C.
• the times for all of these reactions can be varied to accommodate a particular temperature within the expressed ranges, but generally the time is that which is sufficient to produce a satisfactory yield of at least water dispersible chain-extended polyamine with or without, depending on the starting reactant, fatty acid material.
• the reaction is conducted neat if the reactants and reaction product have accommodating viscosities. If one or more viscosities are too high for suitable reaction conditions, the viscosity can be lowered by heating or the use of one or more solvents.
• alcohols and alcohol ethers can be used, whereas with the use of diesters, the reaction can usually be conducted in the neat state.
• the polyamine and chain-extender is reacted or the chair.-extended polyamine is reacted further through what is believed, without limitation of the scope of the invention, to be a partial amidation through reaction with one or more Fatty Acid Materials.
• Suitable nonexclusive examples of these Fatty Acid Materials include: fatty acids, fatty acid esters, fatty acid halides or anhydrides of the acid, where a predominant amount of these Fatty Acid Materials are monovalent in reaction with the chain-extended polyamine to form a condensation product.
• the Fatty Acid Material can be essentially saturated and preferably they are aliphatic of either the straight or branched chain variety.
• fatty acids having from 1 to around 22 carbon atoms and preferably 7 to 12 carbon atoms are preferred.
• Suitable nonexclusive examples of Fatty Acid Material include: acetic acid, pelargonic acid, 2-ethylhexoic, isononanoic, oleic, undecenylenic, caproic, caprylic, octanoic, capric, lauric, and stearic.
• the esters, acid halides, and anhydrides of these acids can also be used.
• fatty acids with a number of carbon atoms of 6 or less When fatty acids with a number of carbon atoms of 6 or less are used, they should be used in a mixture with fatty acids having the higher number of carbon atoms greater than 6 and in a minor amount of that mixture which does not exceed around 50 weight percent of the mixture of fatty acids on a weight percent basis.
• the fatty acids and/or esters and/or acid halides and/or anhydrides can be used in several types of mixtures, although the various components of any one mixture can also be used in the other types of mixtures. All of the mixtures have fatty acids and/or acid halides like acid chlorides and/or esters and/or anhydrides in a predominant amount of the mixture.
• Polymeric fat acids are polymerized fat acids either di eric, trimeric, or higher polymeric forms and thus include the polymerized mixture of acids which usually contains a predominant portion of dimer acids, a small quantity of trimer and higher polymeric forms, and some residual monomer.
• Fat acids are naturally occurring and synthetic monobasic aliphatic acids having hydrocarbon chains of 8 to 24 carbon atoms and include saturated, ethylenically unsaturated, and acetylenically unsaturated acids.
• Another type would include mixtures of saturated and unsaturated Fatty Acid Material where the amount of unsaturated Fatty Acid Material is a minor amount of generally less than 50 weight percent of the mixture.
• acid mixtures such as those obtained by hydrolysis of natural fats and oils are useful. These suitable examples are those derived from coconut oil, corn oil, cottonseed oil, tallow, tall oil, and soybean oil.
• the acids prepared from these oils are various mixtures of approximately 14 to 20 carbon atoms, some of which include both saturated and unsaturated fatty acids including, for example, tetradecanoic, tetradecenoic, hexadecanoic, hexadecenoic, octadecanoic, octadecenioic, octadecadienoic, eicosanoic acids,decanoic, dodecanoic and octadecatrienoic acids. These materials are useful in mixtures with predominantly saturated fatty acids although it is also possible to use straight-chained or branched-chained fatty acids.
• the reaction of any of the aforementioned with the polyamine or preferably the chain-extended polyamines can occur at conditions that vary to some degree depending on the particular reactants.
• the reaction can occur at a temperature ranging from room temperature to elevated temperatures depending on the reactants.
• the temperature can be from room temperature up to around 70°C or so, while for those that are fatty acids, the temperature can be from around 140°C up to around 200°C or more, while preferably with those that are the diester like a succinate, the temperature is in the range from around
• Acid Material usually one mole of alcohol is removed at the lower reaction temperatures and one mole of water can be removed at the higher temperatures.
• the polymeric reaction product of the present invention 5 generally is prepared from the following types of reactants in the generally below-described reactions.
• (VI) is (IV) and/or (V) with moieties of the repeating unit that involve branching such as one or more of the following:
• R is a lower alkyl
• R' is selected from carbonyl, alkyl oxirane and diisocyanate groups
• Q is selected from OR, or halide
• (I) is present in an amount in a slight excess to control the molecular weight.
• the reaction is conducted so that the production and yield of structure V is favored since it is the preferred lubricating material.
• the formation of structure IV is held to a minimum since it is a non-lubricating structure and so that the reaction product has an unreacted amine value. This provides the availability of unreacted secondary nitrogen groups in the reaction product to improve its water dispersibility or solubility;
• the reaction can be done neat although if the viscosity is too high for any particular reactant or reaction product heating or organic solvents like alcohols can be used for dilution.
• the solvent can be other organic solvents than alcohol. For example, where:
• I is: NH 2 -(CH 2 -CH2-NH)3-CH 2 -CH 2 -NH 2 ;
• the reaction is conducted with the sequential addition of I and II and then III to produce mostly Structure V rather than a mixture.
• some of the moieties in the reaction product can be cyclized if a nitrogen with active hydrogens is adjacent to an amide nitrogen.
• the reaction product of the present invention may have present additional materials like poly(ethyleneoxide) in the backbone of the polymer structure to improve water solubility. Also solvents can be present for improved handling and viscosity characteristics. Additionally, one or more antioxidants can be employed to retard yellowing of the dried residue of the reaction product on various substrates.
• additional materials like poly(ethyleneoxide) in the backbone of the polymer structure to improve water solubility.
• solvents can be present for improved handling and viscosity characteristics.
• one or more antioxidants can be employed to retard yellowing of the dried residue of the reaction product on various substrates.
• the polymer reaction product of the present invention finds particular utility as a cationic lubricating substance. Possible uses of this characteristic are had in the fiber manufacturing and chemical treating areas.
• the polymeric reaction product of the present invention can be used by itself or formulated with water to form an aqueous mixture which may also have one or more polymeric film-forming polymers, organo-inorgano coupling agents like organosilane coupling agents, nonionic lubricants, wetting agents, antistatic agents and the like.
• the polymeric reaction product finds particular utility in formulations for chemically treating glass fibers during their formation from molten streams of glass.
• the formulation can be an aqueous sizing formulation where a predominant amount of the formulation is water.
• the amount of the polymeric reaction product that is present can range from around 0.1 up to 15 weight percent of the nonaqueous components of the size and preferably from around 0.5 up to 6 weight percent.
• Optional components include: water soluble poly(oxyethylene), solvents to improve viscosity and handling characteristics, and antioxidants and the like.
• the treated substrate can be dried to remove substantial amounts of the water to produce a dried residue of the formulation.
• the various substrates to which the chain-extended polyamine of the present invention can be applied include fibrous materials like glass fibers and strands and other synthetic and natural fibers and glass plates and beads and the like.
• TEPA Lubricant of Example 1 TEPA was placed in a 1 liter reaction kettle equipped with heating mantel, air stirrer, distillate collector, thermometer, and nitrogen inlet. Diethyl succinate was added to the reactor and a nitrogen purge was started. The mixture was heated with stirring. Condensate (ethanol) began to form when the reaction temperature reached 140°C. The temperature was increased to 160°C as ethanol formation neared completion. Heating was continued until ethanol was no longer generated (approximately one hour). During this time, a total of 98.4 g of distillate was collected. The temperature was reduced to 120°C and the octanoic acid was added.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Textile Engineering (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Geochemistry & Mineralogy (AREA)
• Materials Engineering (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• General Life Sciences & Earth Sciences (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
• Polyamides (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Lubricants (AREA)

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• 1993
  • 1993-06-29 JP JP6502644A patent/JPH07508780A/ja active Pending
  • 1993-06-29 EP EP93915491A patent/EP0650472A1/de not_active Withdrawn
  • 1993-06-29 CA CA002138140A patent/CA2138140A1/en not_active Abandoned
  • 1993-06-29 WO PCT/US1993/006198 patent/WO1994000418A1/en not_active Application Discontinuation
  • 1993-06-30 MX MX9303946A patent/MX9303946A/es not_active Application Discontinuation

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