US3597265A - Fiber lubricants - Google Patents

Fiber lubricants Download PDF

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Publication number
US3597265A
US3597265A US727028A US3597265DA US3597265A US 3597265 A US3597265 A US 3597265A US 727028 A US727028 A US 727028A US 3597265D A US3597265D A US 3597265DA US 3597265 A US3597265 A US 3597265A
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lubricant
strands
fiber
fatty acids
lubricants
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US727028A
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Kenneth T Mecklenborg
Kenneth H Pettengill
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Millennium Petrochemicals Inc
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Emery Oleochemicals LLC
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Assigned to NATIONAL DISTILLERS AND CHEMICAL CORPORATION reassignment NATIONAL DISTILLERS AND CHEMICAL CORPORATION MERGER (SEE DOCUMENT FOR DETAILS). Assignors: BRIDGEPORT ENGRAVERS SUPPLY COMPANY, INCORPORATED, A CORP OF CONNECTICUT, EMERY INDUSTRIES, INC., A CORP OF OHIO, (MERGED INTO), VINCENT BRASS & ALUMINUM CO., A CORP OF MINNESOTA
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • 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
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/255—Oils, waxes, fats or derivatives thereof
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0206—Polyalkylene(poly)amines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/405—Acylated polyalkylene polyamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • Fiber lubricants which comprise partially amidated polyalkylenimines are provided.
  • Exemplary of the lubricant compounds disclosed is the reaction product of a mixture of C to about C fatty acids with a polyethylenimine having a molecular weight of about 1200. The reaction product has a residual amine value of from about 300 to 400.
  • This invention relates to lubricants for fibers, and more particularly to lubricating compositions for use in the manufacture and processing of synthetic fiber strands, such as polyesters, polyacrylics, polyolefins, polyamides, and glass.
  • Still another object of this invention is to provide new and improved lubricants for glass fibers that can be incorporated in conventional glass fiber treating compositions such as sizing compositions.
  • a further object of this invention is to provide a new and improved process for lubricating bundles of continuous filaments.
  • this invention as embodied and broadly described, provides a lubricant for fibers comprising a partially amidated polyalkylenimine.
  • the lubricant is formed by reacting a polyalkylenimine having a molecular weight of at least 800 with a fatty acid to yield an amidated reaction product having a residual amine value of from about 200 to 800.
  • the present inventiOn also provides a process for treating fiber strands which comprises applying to the strands an aqueous composition containing from about 0.01 to 2.0% by weight of the partially amidated polymer lubricant of this invention.
  • the polyalkylenimines that are used to prepare the fiber lubricants of this invention are polymers of alkylenimines containing 2 to about 12 carbons in their alkyl groups, such as ethylenimine, 1,2-pr0pylenimine, l-2-butylenimi-ne, 2,3-butylenimine, and the like.
  • alkylenimines having about 2 to 4 carbon atoms should be used.
  • These alkylenimine polymers have a molecular weight of at least 800 and up to about 50,000 or higher.
  • Polyethylenimine having a molecular weight of around 1200 is a preferred polymer for use in the lubricant compositions of this invention.
  • Commercially available polyethylenimines such as Montrek 12 from the Dowd Chemical Company, which has an average molecular weight of around 1200, can, of course, be used in preparing the present lubricant compositions.
  • the fiber lubricants are prepared by partially amidating a polyalkylenimine with aliphatic fatty acids.
  • fatty acids having from 1 to about 18 carbon atoms and preferably from 2 to 9 carbon atoms produce the best results.
  • Exemplary of the preferred fatty acid amidating agents are acetic acid, pelargonic acid, 2-ethylhexoic, isononanoic, oleic, undecenylenic, caproic, caprylic, capric, and lauric acids. While any of these acids can be used alone, the use of mixtures of fatty acids produce the best results.
  • Mixtures of acids enable use of relatively short chain acids which impart solubility and longer chain acids which impart coatability properties to the lubricant.
  • Preferably l050 equivalent percent of the acids employed should have a carbon atom content of less than 4 and 5090 equivalent percent should have a carbon atom content of greater than about 4.
  • the polyalkylenimines are reacted with the fatty acids in such proportions that from about A to about A of the available amine groups of the polyalkylenimine are amidate with the fatty acid.
  • This reaction yields a partially amidated polyalkylenimine product having an acid value of 0 and a residual amine value of about 200 to about 800, and preferably from about 300 to about 400.
  • Fibers which can be effectively treated with the lubricant of this invention include glass, polyesters such as polyethylene terephthalate, polyolefins such as polypropylene and polyethylene, and polyamides such as nylon.
  • the lubricant is generally dissolved in water to form an aqueous treating composition containing from about 0.01 to 2.0% by weight of the lubricant.
  • Neutralizing amounts of acetic acid can be added to the lubricant to provide a more readily water-soluble compound.
  • the aqueous lubricant solution can be applied to fiber strands in any suitable manner, such as by passing the strands over a roller applicator partially submerged in the solution. It has been found that by applying the lubricant compounds of this invention in the form of an aqueous solution to fiber strands, exceptional internal as well as external lubricity is imparted to the fibers, thereby substantially minimizing fraying, splitting, intertangling, or breaking of the continuous fiber bundles of filaments.
  • the lubricant can be applied in the form of an aqueous solution.
  • the lubricant can be applied as an aqueous solution to the filaments by a roller which forms a part of the guide used to group the attenuated filaments into continuous strands.
  • a continuous lubricant supply can be fed to the roller or guide from a suitable supply tank.
  • the roller can be eliminated and the guide provided with a pad which wipes the lubricant onto the filaments as they pass through the guide.
  • lubricating compounds of this invention can be readily incorporated in aqueous sizing solutions applied to glass fiber strands during their formation and generally immediately after they are formed to improve the integrity and bonding characteristics of the glass fibers.
  • Suitable sizing compositions include aqueous emulsions containing such materials as polyvinyl acetate latex, butadiene-styrene copolymers and polymethylmethacrylates, along with conventional coupling agents, wetting agents, and the like.
  • lubricant compounds of this invention finds its greatest present utility in use in combination with sizing compositions, it is to be understood that the lubricants can be applied to fibers either alone or in combination with other fiber treating solutions, as well as to previously sized fibers.
  • Examples 14 Each of four 300 grams samples of a polyethylenimine sold under the trademark Montrek 12 by the Dow Chemical Company, and having an average molecular weight of about 1200, is charged to a reactor together with a mixture of fatty acids. The reactors are heated to 200 C. with stirring and the Water produced in the reaction is collected. When distillation of the water subsides, the reaction product is sampled until the acid value is 0, indicating that substantially all of the acid has reacted with the polyethylenimine. A nitrogen blanket is used in the reactor to protect the color of the product.
  • the fatty acids used are glacial acetic acid and a fatty acid mixture sold under the tradename Emery 1210 by Emery Industries, Inc., containing 20 to 30% C to C to C 20 to 30% C and 3 to 6% C fatty acids.
  • glacial acetic acid and an essentially pelargonic fatty acid mixture sold under the tradename Emery 1202 by Emery Industries, Inc. containing about 4% C acids, about 94% C acids, and about 2% C fatty acids is used.
  • the following table shows the amount of fatty acid mixture used in each example and the amine value of the partially amidated polyethylenimine product obtained.
  • the lubricants are then applied to continuous glass fiber strands by passing the strands over a roller applicator that is partially submerged in a reservoir of the lubricant solution. Following application of the lubricant, the strands are passed through sundry guides, contact points, and other bearing surfaces that would normally be encountered in a glass fiber processing operation.
  • Example 9 A sizing composition is prepared consisting of an aqueous emulsion neutralized to a pH of about 7 of 4.5% by Weight polyvinylacetate 0.2% by weight of the lubricant of Example 1, 0.5% by weight of vinyl silanol, and the remainder water. Continuous glass fiber strands are then treated with this sizing composition in the manner described in Example 5. The sized strands all exhibit excellent lubricity and resistance to fraying and breaking from internal and external abrasion.
  • Example 10 A polyester fiber, polyethylene terephthalate, is treated with the fiber lubricant of Example 5. The treated yarn exhibits excellent lubricity and resistance to fraying.
  • Glass fiber coated with a lubricant comprising a partially amidated polyalkylenimine having a residual amine value of from about 200 to 800 and formed by reacting a polyalkylenimine having a molecular Weight of 800 to about 50,000 with a fatty acid.
  • the lubricant is the reaction product of a mixture of C to about C fatty acids, and the reaction product has a residual amine value of from about 300 to 400.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Materials Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Surface Treatment Of Glass Fibres Or Filaments (AREA)

Abstract

FIBER LUBRICANTS WHICH COMPRISE PARTIALLY AMIDATED POLYALKYLENIMINES ARE PROVIDED. EXEMPLARY OF THE LUBRICANT COMPOUNDS DISCLOSED IS THE REACTION PRODUCT OF A MIXTURE OF C2 TO ABOUT C18 FATTY ACIDS WITH A POLYETHYLENIMINE HAVING A MOLECULAR WEIGHT OF ABOUT 1200. THE REACTION PRODUCT HAS A RESIDUAL AMINE VALUE OF FROM ABOUT 300 TO 400.

Description

United States Patent 3,597,265 FIBER LUBRICANTS Kenneth T. Mecklenborg and Kenneth H. Pettengill, Cincinnati, Ohio, assignors to Emery Industries, Inc., Cincinnati, Ohio No Drawing. Filed May 6, 1968, Ser. No. 727,028 Int. Cl. C03c 25/02 US. Cl. 117126-GR 2 Claims ABSTRACT OF THE DISCLOSURE Fiber lubricants which comprise partially amidated polyalkylenimines are provided. Exemplary of the lubricant compounds disclosed is the reaction product of a mixture of C to about C fatty acids with a polyethylenimine having a molecular weight of about 1200. The reaction product has a residual amine value of from about 300 to 400.
BACKGROUND OF THE INVENTION This invention relates to lubricants for fibers, and more particularly to lubricating compositions for use in the manufacture and processing of synthetic fiber strands, such as polyesters, polyacrylics, polyolefins, polyamides, and glass.
In the manufacture of fiber strands, a multitude of fine monofilaments, previously drawn from molten baths or solutions of basic fiber compounds, are gathered together to form a continuous strand or bundle of continuous filaments. During their formation, these strands travel at high rates of speed and normally are subjected to destructive abrasive forces caused both by mutual abrasion between the fibers of the strands and by movement of the strands through the guides, eyes, and other machine elements in fiber processing equipment.
It is, therefore, generally necessary to lubricate fiber strands after their formation to prevent abrasive forces from fraying, intertangling, splitting or breaking the strands. Failure to provide proper lubrication can result in frequent and costly shutdowns in fiber processing operations when such damage occurs.
It is therefore a primary object of this invention to provide new and improved lubricants for fibers that impart excellent lubricity to the fibers and thereby prevent damage or destruction of the strands by external and internal abrasive forces normally encountered during processing operations.
Still another object of this invention is to provide new and improved lubricants for glass fibers that can be incorporated in conventional glass fiber treating compositions such as sizing compositions.
A further object of this invention is to provide a new and improved process for lubricating bundles of continuous filaments.
Additional objects and advantages will be set forth in part in the description which follows and in part will be obvious from the description or may be learned by practice of the invention, the objects and advantages being realized and attained by means of the compositions, processes, and improvements particularly pointed out in the appended claims.
e ICC DESCRIPTION OF THE INVENTION To achieve the foregoing objects and in accordance with its purpose, this invention as embodied and broadly described, provides a lubricant for fibers comprising a partially amidated polyalkylenimine. The lubricant is formed by reacting a polyalkylenimine having a molecular weight of at least 800 with a fatty acid to yield an amidated reaction product having a residual amine value of from about 200 to 800.
The present inventiOn also provides a process for treating fiber strands which comprises applying to the strands an aqueous composition containing from about 0.01 to 2.0% by weight of the partially amidated polymer lubricant of this invention.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory but are not restrictive of the invention.
The polyalkylenimines that are used to prepare the fiber lubricants of this invention are polymers of alkylenimines containing 2 to about 12 carbons in their alkyl groups, such as ethylenimine, 1,2-pr0pylenimine, l-2-butylenimi-ne, 2,3-butylenimine, and the like. Preferably, alkylenimines having about 2 to 4 carbon atoms should be used. These alkylenimine polymers have a molecular weight of at least 800 and up to about 50,000 or higher.
Polyethylenimine, having a molecular weight of around 1200 is a preferred polymer for use in the lubricant compositions of this invention. Commercially available polyethylenimines, such as Montrek 12 from the Dowd Chemical Company, which has an average molecular weight of around 1200, can, of course, be used in preparing the present lubricant compositions.
In accordance with this invention the fiber lubricants are prepared by partially amidating a polyalkylenimine with aliphatic fatty acids. Although a wide variety of fatty acids can be used, fatty acids having from 1 to about 18 carbon atoms and preferably from 2 to 9 carbon atoms produce the best results.
Exemplary of the preferred fatty acid amidating agents are acetic acid, pelargonic acid, 2-ethylhexoic, isononanoic, oleic, undecenylenic, caproic, caprylic, capric, and lauric acids. While any of these acids can be used alone, the use of mixtures of fatty acids produce the best results. The term fatty acid as used in the present specification and claims, therefore, is intended to include mixtures of fatty acids. Mixtures of acids enable use of relatively short chain acids which impart solubility and longer chain acids which impart coatability properties to the lubricant. Preferably l050 equivalent percent of the acids employed should have a carbon atom content of less than 4 and 5090 equivalent percent should have a carbon atom content of greater than about 4.
In accordance with this invention the polyalkylenimines are reacted with the fatty acids in such proportions that from about A to about A of the available amine groups of the polyalkylenimine are amidate with the fatty acid. This reaction yields a partially amidated polyalkylenimine product having an acid value of 0 and a residual amine value of about 200 to about 800, and preferably from about 300 to about 400.
Fibers which can be effectively treated with the lubricant of this invention include glass, polyesters such as polyethylene terephthalate, polyolefins such as polypropylene and polyethylene, and polyamides such as nylon.
In treating fibers with the lubricants of this invention, the lubricant is generally dissolved in water to form an aqueous treating composition containing from about 0.01 to 2.0% by weight of the lubricant. Neutralizing amounts of acetic acid can be added to the lubricant to provide a more readily water-soluble compound.
The aqueous lubricant solution can be applied to fiber strands in any suitable manner, such as by passing the strands over a roller applicator partially submerged in the solution. It has been found that by applying the lubricant compounds of this invention in the form of an aqueous solution to fiber strands, exceptional internal as well as external lubricity is imparted to the fibers, thereby substantially minimizing fraying, splitting, intertangling, or breaking of the continuous fiber bundles of filaments.
In the manufacture of glass, polyester, polyolefins, and polyamide strands, the lubricant can be applied in the form of an aqueous solution. For example, where molten streams of glass issue continuously from a plurality of orifices and are rapidly attenuated into fine glass filaments by means of a winding spindle, the lubricant can be applied as an aqueous solution to the filaments by a roller which forms a part of the guide used to group the attenuated filaments into continuous strands. A continuous lubricant supply can be fed to the roller or guide from a suitable supply tank. Alternatively, the roller can be eliminated and the guide provided with a pad which wipes the lubricant onto the filaments as they pass through the guide.
The lubricating compounds of this invention can be readily incorporated in aqueous sizing solutions applied to glass fiber strands during their formation and generally immediately after they are formed to improve the integrity and bonding characteristics of the glass fibers. Suitable sizing compositions include aqueous emulsions containing such materials as polyvinyl acetate latex, butadiene-styrene copolymers and polymethylmethacrylates, along with conventional coupling agents, wetting agents, and the like.
While use of the lubricant compounds of this invention finds its greatest present utility in use in combination with sizing compositions, it is to be understood that the lubricants can be applied to fibers either alone or in combination with other fiber treating solutions, as well as to previously sized fibers.
The examples are merely illustrative and are not to be understood as limiting the scope and underlying principles of the invention in any Way. All percentages referred to herein are by weight based on the total weight of the treating compositions unless otherwise specifically indicated.
Examples 14 Each of four 300 grams samples of a polyethylenimine sold under the trademark Montrek 12 by the Dow Chemical Company, and having an average molecular weight of about 1200, is charged to a reactor together with a mixture of fatty acids. The reactors are heated to 200 C. with stirring and the Water produced in the reaction is collected. When distillation of the water subsides, the reaction product is sampled until the acid value is 0, indicating that substantially all of the acid has reacted with the polyethylenimine. A nitrogen blanket is used in the reactor to protect the color of the product.
In Examples 1 and 2, the fatty acids used are glacial acetic acid and a fatty acid mixture sold under the tradename Emery 1210 by Emery Industries, Inc., containing 20 to 30% C to C to C 20 to 30% C and 3 to 6% C fatty acids. In Examples 3 and 4, glacial acetic acid and an essentially pelargonic fatty acid mixture sold under the tradename Emery 1202 by Emery Industries, Inc., containing about 4% C acids, about 94% C acids, and about 2% C fatty acids is used.
The following table shows the amount of fatty acid mixture used in each example and the amine value of the partially amidated polyethylenimine product obtained.
TABLE I Amine value of Examples 5-8 The partially amidated polyethylenimine products of each of Examples l-4 are neutralized with acetic acid to a pH of about 6 to 7, and dissolved in Water to provide 0.5% aqueous solutions.
The lubricants are then applied to continuous glass fiber strands by passing the strands over a roller applicator that is partially submerged in a reservoir of the lubricant solution. Following application of the lubricant, the strands are passed through sundry guides, contact points, and other bearing surfaces that would normally be encountered in a glass fiber processing operation.
The strands lubricated with the products of this invention and yarns subsequently made therefrom all exhibit excellent lubricity with a minimum of fraying or broken ends.
Example 9 A sizing composition is prepared consisting of an aqueous emulsion neutralized to a pH of about 7 of 4.5% by Weight polyvinylacetate 0.2% by weight of the lubricant of Example 1, 0.5% by weight of vinyl silanol, and the remainder water. Continuous glass fiber strands are then treated with this sizing composition in the manner described in Example 5. The sized strands all exhibit excellent lubricity and resistance to fraying and breaking from internal and external abrasion.
Example 10 A polyester fiber, polyethylene terephthalate, is treated with the fiber lubricant of Example 5. The treated yarn exhibits excellent lubricity and resistance to fraying.
The invention in its broader aspects is not limited to the specific details shown and described and departures may be made from such details Within the spirit and scope of the accompanying claims without departing from the principles of the invention and without sacrificing its chief advantages.
An emulsion containing about 50 solids sold under the trademark Elvacet by E. I. du Pont de Nemours & Company.
What is claimed is:
1. Glass fiber coated with a lubricant comprising a partially amidated polyalkylenimine having a residual amine value of from about 200 to 800 and formed by reacting a polyalkylenimine having a molecular Weight of 800 to about 50,000 with a fatty acid.
2. The invention of claim 1 in which the lubricant is the reaction product of a mixture of C to about C fatty acids, and the reaction product has a residual amine value of from about 300 to 400.
References Cited UNITED STATES PATENTS 3,462,254 8/1969 Marzocchi et al. ll7l26X 3,346,489 10/1967 Dickson et al 2528.8X 3,198,754 8/1965 Ahlbrecht et al 260-2 2,272,489 2/ 1942 Ulrich 260-2X DONALD E. CZAJA, Primary Examiner C. W. IVY, Assistant Examiner US. Cl. X.R.
117-l39.5A; 2602EN, 18N, 29.6NR, 29.7NR
US727028A 1968-05-06 1968-05-06 Fiber lubricants Expired - Lifetime US3597265A (en)

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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772870A (en) * 1971-06-07 1973-11-20 Owens Corning Fiberglass Corp Sizing composition and glass fibers sized therewith
US4104228A (en) * 1976-12-27 1978-08-01 The Dow Chemical Company Linear, partially deacylated poly(N-acyl)alkylenimines as tannin migration inhibitors
US4248935A (en) * 1978-08-21 1981-02-03 Ppg Industries, Inc. Storage stable polyolefin compatible non-crosslinking size for fiber glass strands
US4358501A (en) * 1978-08-14 1982-11-09 Ppg Industries, Inc. Storage stable polyolefin compatible size for fiber glass strands
US4413085A (en) * 1978-08-21 1983-11-01 Ppg Industries, Inc. Storage stable polyolefin compatible non-crosslinking size for fiber glass strands
US4637956A (en) * 1985-03-29 1987-01-20 Ppg Industries, Inc. Sized glass fibers and reinforced polymers containing same
US4808478A (en) * 1986-09-05 1989-02-28 Ppg Industries, Inc. Chemically treated glass fibers for reinforcing thermosetting polymers
US4927869A (en) * 1988-09-15 1990-05-22 Ppg Industries, Inc. Chemically treated glass fibers for reinforcing polymers
US5089188A (en) * 1989-01-04 1992-02-18 Ppg Industries, Inc. Spinning of sol gel siliceous-containing fibers with wet coagulation
US5141802A (en) * 1988-07-15 1992-08-25 Ppg Industries, Inc. Chemically treated shapes, fillers and reinforcement for polymer matrices
US5269952A (en) * 1992-12-21 1993-12-14 E. I. Du Pont De Nemours And Company Antistatic finish for dyeable surfactant-containing poly(m-phenylene isophthalamide) fibers
US5354829A (en) * 1992-06-30 1994-10-11 Ppg Industries, Inc. Silylated polyamine polymers and a method of treating fibers
US5393379A (en) * 1990-12-05 1995-02-28 Ppg Industries, Inc. Wet laid fiberous thermoplastic material and aqueous dispersion for producing same
US5393335A (en) * 1993-04-23 1995-02-28 Ppg Industries, Inc. Starch-oil sizing for glass fibers
US5437928A (en) * 1993-10-29 1995-08-01 Ppg Industries, Inc. Glass fiber size and mat
US5466528A (en) * 1992-08-21 1995-11-14 Ppg Industries, Inc. Chemically treated glass type substrates with vinyl polymer compatibility
US6139958A (en) * 1988-03-31 2000-10-31 Ppg Industries Ohio, Inc. Chemically treated glass fibers for reinforcing thermosetting polymer matrices
WO2001049627A1 (en) 1999-12-29 2001-07-12 Owens Corning System for preparing glass fiber pellets having low discoloration
WO2001068739A1 (en) * 2000-03-13 2001-09-20 Cognis Corporation Color-stable polyalkyleneimine derivatives, fiberglass lubricants containing the same and processes for producing the same
WO2001083394A1 (en) 2000-04-25 2001-11-08 Owens Corning Loose-fill insulation with improved recoverability
WO2001094447A1 (en) * 2000-06-08 2001-12-13 Cognis Corporation Water-dispersible, hydrophobic polyalkyleneimine polyamide fiberglass lubricant, process for producing the same, and method of use therefor
WO2001096655A1 (en) * 2000-06-13 2001-12-20 Basf Aktiengesellschaft Use of acylated polyamines for the modification of surfaces
WO2003053875A2 (en) 2001-12-21 2003-07-03 Owens Corning Composites S.P.R.L. System for preparing glass fiber pellets having low discoloration
JP2006089734A (en) * 2004-08-25 2006-04-06 Toray Ind Inc Thermoplastic resin composition
US20170298184A1 (en) * 2016-02-17 2017-10-19 Saint-Gobain Isover Needling Additive for the Manufacture of Needle Felts of Mineral Wool and Needle Felt Manufactured Therewith
WO2024068700A1 (en) 2022-09-29 2024-04-04 Basf Se Improving adhesion of fibre materials in rubber composites

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Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772870A (en) * 1971-06-07 1973-11-20 Owens Corning Fiberglass Corp Sizing composition and glass fibers sized therewith
US4104228A (en) * 1976-12-27 1978-08-01 The Dow Chemical Company Linear, partially deacylated poly(N-acyl)alkylenimines as tannin migration inhibitors
US4358501A (en) * 1978-08-14 1982-11-09 Ppg Industries, Inc. Storage stable polyolefin compatible size for fiber glass strands
US4248935A (en) * 1978-08-21 1981-02-03 Ppg Industries, Inc. Storage stable polyolefin compatible non-crosslinking size for fiber glass strands
US4413085A (en) * 1978-08-21 1983-11-01 Ppg Industries, Inc. Storage stable polyolefin compatible non-crosslinking size for fiber glass strands
US4637956A (en) * 1985-03-29 1987-01-20 Ppg Industries, Inc. Sized glass fibers and reinforced polymers containing same
US4808478A (en) * 1986-09-05 1989-02-28 Ppg Industries, Inc. Chemically treated glass fibers for reinforcing thermosetting polymers
US6139958A (en) * 1988-03-31 2000-10-31 Ppg Industries Ohio, Inc. Chemically treated glass fibers for reinforcing thermosetting polymer matrices
US5141802A (en) * 1988-07-15 1992-08-25 Ppg Industries, Inc. Chemically treated shapes, fillers and reinforcement for polymer matrices
US4927869A (en) * 1988-09-15 1990-05-22 Ppg Industries, Inc. Chemically treated glass fibers for reinforcing polymers
US5089188A (en) * 1989-01-04 1992-02-18 Ppg Industries, Inc. Spinning of sol gel siliceous-containing fibers with wet coagulation
US5393379A (en) * 1990-12-05 1995-02-28 Ppg Industries, Inc. Wet laid fiberous thermoplastic material and aqueous dispersion for producing same
US5354829A (en) * 1992-06-30 1994-10-11 Ppg Industries, Inc. Silylated polyamine polymers and a method of treating fibers
EP0705861A1 (en) * 1992-06-30 1996-04-10 Ppg Industries, Inc. Silylated lubricant with and without other components and on substrates and method
US5466528A (en) * 1992-08-21 1995-11-14 Ppg Industries, Inc. Chemically treated glass type substrates with vinyl polymer compatibility
WO1994015012A1 (en) * 1992-12-21 1994-07-07 E.I. Du Pont De Nemours And Company Antistatic finish for dyeable surfactant-containing poly(m-pheny lene isophthalamide) fibers
US5269952A (en) * 1992-12-21 1993-12-14 E. I. Du Pont De Nemours And Company Antistatic finish for dyeable surfactant-containing poly(m-phenylene isophthalamide) fibers
US5393335A (en) * 1993-04-23 1995-02-28 Ppg Industries, Inc. Starch-oil sizing for glass fibers
US5648169A (en) * 1993-10-29 1997-07-15 Ppg Industries, Inc. Glass fiber size and mat
US5437928A (en) * 1993-10-29 1995-08-01 Ppg Industries, Inc. Glass fiber size and mat
WO2001049627A1 (en) 1999-12-29 2001-07-12 Owens Corning System for preparing glass fiber pellets having low discoloration
US6399741B1 (en) * 2000-03-13 2002-06-04 Cognis Corporation Color-stable polyalkyleneimine derivatives, fiberglass lubricants containing the same and processes for producing the same
WO2001068739A1 (en) * 2000-03-13 2001-09-20 Cognis Corporation Color-stable polyalkyleneimine derivatives, fiberglass lubricants containing the same and processes for producing the same
WO2001083394A1 (en) 2000-04-25 2001-11-08 Owens Corning Loose-fill insulation with improved recoverability
US6562257B1 (en) 2000-04-25 2003-05-13 Owens Corning Fiberglas Technology, Inc. Loose-fill insulation with improved recoverability
WO2001094447A1 (en) * 2000-06-08 2001-12-13 Cognis Corporation Water-dispersible, hydrophobic polyalkyleneimine polyamide fiberglass lubricant, process for producing the same, and method of use therefor
US20020017627A1 (en) * 2000-06-08 2002-02-14 Fry Douglas F. Water-dispersible, hydrophobic polyalkyleneimine polyamide fiberglass lubricant, process for producing the same, and method of use therefor
US7026435B2 (en) 2000-06-08 2006-04-11 Cognis Corporation Water-dispersible, hydrophobic polyalkyleneimine polyamide fiberglass lubricant, process for producing the same, and method of use therefor
WO2001096655A1 (en) * 2000-06-13 2001-12-20 Basf Aktiengesellschaft Use of acylated polyamines for the modification of surfaces
US20040018357A1 (en) * 2000-06-13 2004-01-29 Valerie Andre Use of acylated polyamines for modifying surfaces
JP2004503667A (en) * 2000-06-13 2004-02-05 ビーエーエスエフ　アクチェンゲゼルシャフト Use of acylated polyamines to modify surfaces
US6984451B2 (en) 2000-06-13 2006-01-10 Basf Aktiengesellschaft Use of acylated polyamines for the modification of surfaces
JP4886155B2 (en) * 2000-06-13 2012-02-29 ビーエーエスエフ ソシエタス・ヨーロピア Use of acylated polyamines to modify surfaces
WO2003053875A2 (en) 2001-12-21 2003-07-03 Owens Corning Composites S.P.R.L. System for preparing glass fiber pellets having low discoloration
JP2006089734A (en) * 2004-08-25 2006-04-06 Toray Ind Inc Thermoplastic resin composition
US20170298184A1 (en) * 2016-02-17 2017-10-19 Saint-Gobain Isover Needling Additive for the Manufacture of Needle Felts of Mineral Wool and Needle Felt Manufactured Therewith
WO2024068700A1 (en) 2022-09-29 2024-04-04 Basf Se Improving adhesion of fibre materials in rubber composites

Also Published As

Publication number Publication date
SE366071B (en) 1974-04-08
BE732534A (en) 1969-11-05
DE1923061A1 (en) 1969-11-20
FR2007902A1 (en) 1970-01-16
NL6906864A (en) 1969-11-10
GB1264496A (en) 1972-02-23
FR2007902B1 (en) 1973-12-21

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