US3226179A - Papermaker's felt, woven fabrics and fibers of wool modified with an aldehyde - 4,4 - bis(4 - hydroxy phenyl) pentanoic acid reaction product and the production thereof - Google Patents

Papermaker's felt, woven fabrics and fibers of wool modified with an aldehyde - 4,4 - bis(4 - hydroxy phenyl) pentanoic acid reaction product and the production thereof Download PDF

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US3226179A
US3226179A US227540A US22754062A US3226179A US 3226179 A US3226179 A US 3226179A US 227540 A US227540 A US 227540A US 22754062 A US22754062 A US 22754062A US 3226179 A US3226179 A US 3226179A
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wool
fibers
formaldehyde
felt
bis
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Arthur E Manasian
Lehner George
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Huyck Corp
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Huyck Corp
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Priority to US245393A priority patent/US3292992A/en
Priority to GB31509/63A priority patent/GB1029803A/en
Priority to FR946031A priority patent/FR1377382A/fr
Priority to NL297429D priority patent/NL297429A/xx
Priority to DE19631444074 priority patent/DE1444074B1/de
Priority to SE9783/63A priority patent/SE309959B/xx
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Priority to SE2372/67A priority patent/SE309767B/xx
Assigned to HUYCK CORPORATION A CORP. OF NY. reassignment HUYCK CORPORATION A CORP. OF NY. MERGER (SEE DOCUMENT FOR DETAILS). EFFECTIVE 10-24-80 STATE OF DEL. Assignors: HUYCK CORPORATION (MERGED INTO) BTR FABRICS (USA) AND CHANGED INTO
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    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D233/28Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D237/00Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/18Sulfur atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/58Two sulfur atoms
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    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/86Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/93Sulfur atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40Benzopyrazines
    • C07D241/44Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
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    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40Nitrogen atoms
    • C07D251/48Two nitrogen atoms
    • C07D251/52Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
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    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40Nitrogen atoms
    • C07D251/54Three nitrogen atoms
    • C07D251/56Preparation of melamine
    • C07D251/58Preparation of melamine from cyanamide, dicyanamide or calcium cyanamide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D271/00Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/101,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/1131,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36Sulfur atoms
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    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/68Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07D279/041,3-Thiazines; Hydrogenated 1,3-thiazines
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    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/1251,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/12Aldehydes; Ketones
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/152Treating 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 oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188Monocarboxylic acids; Anhydrides, halides or salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/207Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41Phenol-aldehyde or phenol-ketone resins

Definitions

  • This invention relates to a process for treating protein materials and to the product resulting therefrom, and more particularly relates to the process and product of treating wool.
  • Protein materials consist of protein molecules made up of various amino acids linked through amido linkages to form long chain structures called polypeptides. Individual properties of proteinaceous materials are caused by variations in the proportion and arrangement of the different amino acids. Other factors affecting properties are variations in chain lengths, degree of cross-linking and the presence of other groups in linkages other than the basic peptide linkages. In many cases protein fibers are deficient in their tensile properties because there are insufficient cross-linkages between the peptide chains or because the linkages present in the dry fiber are easily broken.
  • Wool and other protein material can be modified to advantage using precondensates of polyhydric phenols and formaldehyde.
  • protein materials, particularly leather can be modified with water soluble or solvent soluble condensation products of phenols and aldehydes. DihydroXy and trihydroxy derivatives of benzene and their substitution products can be used effectively with aldehydes to modify proteinaceous materials. Monohydric phenols having sufficient reactivity will combine with formaldehyde and wool resulting in a weight increase and possibly some change in properties.
  • the known reactants which produce the desired improvements in properties also have the undesirable result of adversely affecting the color of the treated protein material. The color may be imparted to the material when heated or may arise after use or upon exposure to heat or light.
  • This invention is useful as a shrinkproofing and wash and wear treatment for woolen clothing and other fabrics.
  • the invention may also be used as a modifier of felt hats and as a leather tanning agent.
  • the known processes using phenolic resins for shrink-proofing or applying wash and wear treatment to woolen clothing and other fabrics result in an undesirable discoloration of the material treated.
  • the present invention treats such materials without causing discoloration.
  • a papermarkers felt is a woven fabric, usually wool, which is usually fulled after weaving to form a firm fabric of specific desired dimensions. Having been fulled to predetermined dimensions, it is essential to the successful use of the felt that it maintain these dimensions as closely as possible.
  • Such felts are employed to convey wet paper from a web forming device to and through apparatus used in the paper making process.
  • the felt is subject to much abrasion and chemical action in use and has a relatively short life. It is essential that the felt have high tensile strength because it is subject to much ICC stress and stretching in the paper making apparatus.
  • the felt must have a high degree of porosity to allow water to drain freely through the felt as it passes through the various paper making steps.
  • the felt must be easily cleanable because the felts tend to fill up with foreign matter and small fibers of pulp which must be regularly removed. Satisfactory drainage of water from the wet pulp must be maintained so that the speed of the paper making process is not reduced because of insufficient water removal from the wet pulp. To meet all of these requirements the wool fibers used in papermakers felts must be chosen without regard to cost. Thus the life of the felt is a substantial factor in the cost of producing paper and other articles made from wet pulp.
  • the objects of this invention are achieved by treating a proteinaceous material with 4,4-bis(4-hydroXy-phenyl) pentanoic acid, which is also known as diphenolic acid, and an aldehyde.
  • 4,4-bis(4-hydroXy-phenyl) pentanoic acid which is also known as diphenolic acid
  • aldehyde is the preferred aldehyde, but acetaldehyde, or benzaldehyde, or propionaldehyde may be substituted for formaldehyde.
  • the diphenolic acid has a structural formula as follows:
  • This invention relates primarily to the treatment of protein fibers to cause chemical modifications so that in an atmosphere of high humidity the treated protein fiber behaves more like a dry fiber. When completely saturated with water the treated fiber has increased resistance to extension (stretching).
  • a fabric made from treated fibers has significantly increased wear resistance as measured by conventional laboratory testers or by practical use.
  • Treated fibers, such as wool also have improved resistance to size increase under applied stress and improved resistance to size decrease caused by felting.
  • the microbiological resistance of treated fabric is greater than that of untreated fabric.
  • the process of this invention may be carried out by immersing the protein fiber to be treated in a solution of diphenolic acid and formaldehyde which have not had time to polymerize substantially.
  • the treatment is not effective if the reactants polymerize prior to contacting the protein.
  • After removal from the solution the treated fiber is rinsed with warm Water and dried.
  • the temperature range of the process is determined by the solubility of the diphenolic acid in the solvent system used.
  • the process may thus be conducted within a wide range of temperatures, such as from 50 to 100 C. In treating wool, however, we prefer to carry out the reaction at temperatures between about 60 C. and 100 C.
  • the pH of solution may be varied widely, such as from about 2 to 9. If the pH is below about 2, the proteinaceous fibers tend to decompose. If the pH is above about 9, improvement in fiber properties is negligible. Above a pH of about 10, fibers also tend to decompose under conditions of the treatment. A pH between 4.5 and 7.0 has been found particularly satisfactory. The preferred pH range is from 5.5 to 6.5. In practice, a pH of about 5.5 results from the use of diphenolic acid without an added buffer.
  • diphenolic acid concentrations are between about 0.02 and 0.08 mole per liter (M). It has been found that above a concentration of about 0.08 M, little improvement in the properties of treated materials is observed, although their weight continues to increase.
  • the molar ratio of formaldehyde to diphenolic acid has been varied from 1:2 to 4:1. Higher concentrations of formaldehyde tend to produce a tensilely weaker product than low concentrations. In practice, it is preferred to use a formaldehyde to diphenolic acid molar ratio of about 2:1.
  • the treating solution to protein ratios may be varied from 0.6:1 to 50:1. However, it is preferred that the ratio be maintained between about 8:1 to 40:1. Best results have been obtained within a solution to protein ratio of about 16 to 1.
  • the treated product is heavier than the starting protein material.
  • the resulting weight increase rises as the availability and concentration of diphenolic acid increase.
  • the maximum effective weight increase is about 20% at a diphenolic acid molar concentration of 0.08 M using a 16:1 solution to protein ratio. Weight increases beyond about 20% do not result in an improvement in properties.
  • the process may be used to modify a mixture of protein fibers or a mixture of protein and non-protein fibers. Because the reaction rnodifies only the protein fibers, the treatment may be employed on fabric containing synthetic and other natural fibers without regard to the percentage of protein fiber in the fabric. If however, the fabric contains fibers, such as nylon, which react with one or more of the reactants, due consideration must be given to such reaction in order that a proper level of modification of the protein fiber is reached. Fabrics containing at least 25% proteinaceous material, preferably wool, and up to 75% of a synthetic, such as nylon or Dacron (polyester), by weight, have been treated with no evidence of a limit having been reached, while observing the foregoing cautions.
  • a synthetic such as nylon or Dacron (polyester)
  • Fabrics such as for papermakers felts, containing at least about 25 wool, provide a suitable capability of fulling and felting and, when treated in accordance with the invention, have enhanced resistance to wear, microbiological attack, and other enhanced properties over those of the untreated fabric.
  • Those fabrics containing at least about 40% wool are particularly enhanced in their properties by the treatment of the invention.
  • nylon will react with one or more of the diphenolic acid or aldehyde reactants, and therefore sufficient amounts of reactants are desirably employed to react with it; other synthetics, such as Dacron, react only slightly, if at all, and when employing such synthetics, little or none of the reactants are needed to react with the synthetic component of the substrate.
  • Tables I-VII The nature of the improvements made possible by the process of the invention and the resultant product is indicated in Tables I-VII below.
  • Table I shows the modifications produced in wool by varying the concentration of the diphenolic acid, the formaldehyde to diphenolic acid molar ratio being held constant at 2:1.
  • W001 was used as the protein fiber at a treatment solution to wool ratio of 16:1.
  • the diphenolic acid was dissolved in an aqueous solution of 5% by solution volume of isopropanol.
  • the treatment of the wool in the solution of diphenolic acid and formaldehyde was carried out for one hour at 74 C.; after which the wool was rinsed and dried for one hour at 105 C.
  • the Percent Pickup corresponds to the weight increase of wool during treatment and was determined by comparing the dry weight of the treated product with the dry untreated wool used.
  • the Pounds Tensile is the breaking strength of the material and was determined by placing a one inch wide strip of material in a standard tensile tester and recording the break point.
  • the Work Index is a comparison of the force required to stretch treated wool fabrics with the force required to stretch the same fibers prior to treatment.
  • the force required to elongate by 20% a single fiber of material, before and after treatment, is graphed. Force is charted as the ordinate; elongation is charted as the abscissa. The areas under the two resultant curves are compared to determine the Work Index.
  • the Standard is untreated wool similar in all other respects to the treated wool.
  • Table I shows that above a diphenolic acid concentration of 0.060.07 M, the increase in weight of the protein fiber does not result in any further improvement in fiber properties as indicated by the Work Index.
  • Table I also shows that the percent of weight pickup increases as the rnolarity of the diphenolic acid increases.
  • the increase in Percent Pickup is directly proportional to the amount of diphenolic acid that is available for reaction.
  • Table II shows the results of using a formaldehyde to diphenolic acid ratio of 1:2. The procedures were otherwise the same as used in the tests set forth in Table I.
  • the Percent Pickup in Table II varies directly as the amount of diphenolic acid available for reaction.
  • Table III shows the effect of a 4:1 formaldehyde to diphenolic acid molar ratio.
  • the solutions used in the preparation of the data of Table III were made by dissolving the diphenolic acid in 50 ml. of isopropanol with rapid stirring at room temperature. The resulting solution was added to 950 ml. of water preheated to 70 C. to make a treating solution of the desired molarity. Wool felts were added to the solution; the formaldehyde was then added, and the reaction was continued with agitation for one hour. The felts were then removed, washed with cold tap water and dried for one hour at C. The solution to wool ratio used was 16 to 1; the pH of the solution was 5.5.
  • ventiom I may b l d d from th t bl th t ro-
  • the Strips used were about 0116 inch across. and about 8 Ieinaceous material treated with the process of the into 10 inches long-
  • the Standard Soil Was P p and vention has color stability equal to or better than that the test was run according to ASTM D 684-45T Test 7 of th pi-oteinaeeous t i l it lf, for Resistance of Textile Materials to Microorganisms. I Order more l l t di l th nature of th The water content of the soil was adjusted to 30%.
  • f 11 Example I The Bacillus subtilus test was carried out as o ows. The weight of the wool samples was determined and a i fi of 9 g .qf y; g 5 corresponding amount of prepared broth was weighed e compnsmg. S an m y 0 W00 an WhlCh had been fulled, 1n 80 parts of rsopropanol were out for each of the samples. The sterilized broth was dissolved 13 6 rt f h d th then inoculated with Bacillus subtilus bacteria as supplied Solution ad 2 Z 2 ⁇ 1.
  • the felt was found to have infor the predetermined time shown in Table VI.
  • the creased in Wei b 7 Th d t broth was maintained in the bacterial oven as in the extend individuil t e fi B g 3 previous soil burial tests at 30 C. during this time.
  • the b a mximat 1 g y percen d g g strips were removed from the broth, sterilized and their g gf f g requlre t 3 tensile strength determined.
  • the final tensile strength The roduct g th y i' was then compared to the tensile strength before the f It O at WOO en paperexposure to the Bacillus subtilus.
  • Example II The procedure of Example I was repeated except that Percent Tensile strength Retained the diphenolic acid was dissolved in 1600 parts of Water Time at 96 C., no isopropanol being used. The water was Untreated Treated then cooled to 74 C., and treatment of the fabric was carried out as in Example I. A weight increase of 6.8% so Burial Test: resulted. The average force to extend a fiber by twenty wigg percent was increased by 91.9%. The ultimate tensile 3WkS 0 19 Strength of the treated fabric was of that of the a g Test! original fabric. The product was the color of the natural ys 15 92 21 days 15 75 fabrlc and did not dlscolor during use.
  • Table VII shows the color of the treated ma- Example terial to be as stable as the untreated material upon 5 A stock dyed woolen blanket fabric, weighing 60 aging and when exposed to light and heat. pounds was treated in a piece dye kettle with a solution The stability of color to ultraviolet light was determade up of 13.75 pounds of diphenolic acid, 8 pounds mined by exposing an untreated woolen sample and a of 37% formaldehyde solution, and 12.5 gallons of methatreated woolen sample about an inch wide by 8 inches nol in gallons of water. The treatment was conlong to an ultraviolet lamp at a distance of about one 7 tinned for one hour at F. The treated blanket foot. The results are shown in Table VII.
  • a solution of isopropanol in water was prepared in which the isopropanol was equal to of the solution volume.
  • the total volume used was 800 cc. This was equivalent to a 16:1 liquor to wool ratio.
  • Example V The procedure of Example IV was repeated except that acetaldehyde was substituted for the benzaldehyde. Upon examination, the color of the wool was found to be unchanged by the treatment; the color did not change during use. The Percent Pickup was found to be 6.4. The Work Index was 102.4, and the Pounds Tensile was 117.5 as compared with the Standard of 120.
  • Example VI The procedure of Example IV was repeated, except that propionaldehyde was substituted for the benzaldehyde. Upon examination of the product, the color of the original wool was found to be unchanged. The color did not change during use. The Percent Pickup was 6.0%. The Work Index was 101.1, and the Pounds Tensile was 126.4 against a Standard of 120.
  • Example VII The treatment of a woven fabric containing 55% wool and 45% nylon was carried out as follows. In 80 parts of isopropanol were dissolved 13.6 parts of diphenolic acid. The solution was added to 1520 parts of water at 60 C. To this solution were added 2.9 parts of formaldehyde. Into the resulting solution were immersed 100 parts of the woven fabric containing 55% wool and 45% nylon. Treatment was carried out for one hour at 60 C. The fabric was then rinsed with warm water and dried. The fabric was found to have a dry weight increase of 8.4%.
  • Example VIII The procedure of Example VII was repeated except that 100 parts of a woven fabric containing 50% wool, 25% nylon and 25 Dacron, a polyester resin, were used. The dry weight increase after treatment was found to be 7.1%.
  • Example IX The procedure of Example VII was repeated except that 100 parts of woven fabric containing 55% wool and 45 Dacron, a polyester resin, were used. The dry weight increase after treatment was found to be 5.0%.
  • a process for treating keratin fibers comprising immersing keratin fibers in an aqueous solution of 4,4-bis- (4-hydroxy phenyl) pentanoic acid and an aldehyde selected from the class consisting of formaldehyde, acetaldehyde, benzaldehyde and propionaldehyde, and drying said keratin fibers, whereby the chemical and physical properties of the keratin fibers are improved without changing the color of said fibers.
  • a process for treating keratin fibers comprising immersing keratin fibers in an aqueous solution of 4,4-bis (4- hydroxy phenyl) pentanoic acid and formaldehyde, and drying said keratin fibers, whereby the chemical and physical properties of the keratin fibers are improved without changing the color of said fibers.
  • a process for treating keratin fibers comprising dissolving 4,4-bis(4-hydroxy phenyl) pentanoic acid in water heated to at least about C., adding formaldehyde in a ration to said acid of between about 1:2 to 4: l, immersing the keratin fibers to be treated in the solution, and drying said keratin fibers, whereby the dimensional stability and bacterial resistance of said keratin fibers are increased without changing the color of said keratin fibers.
  • a process for treating keratin fibers comprising dissolving 4,4-bis(4-hydroxy phenyl) pentanoic acid and formaldehyde in an aqueous solution of alcohol, having a pH of between about 2 to 9, said formaldehyde being present in a ratio of 1:2 to 4:1 to said acid, heating said solution to between about 50 to C., immersing the keratin fibers in said solution for about one hour while maintaining said temperature, and drying said keratin fibers, whereby the dimensional stability and bacterial resistance are increased without changing the color of the keratin fibers.
  • a process for treating keratin fibers comprising dissolving 4,4-bis(4-hydroxy phenyl) pentanoic acid and formaldehyde in an aqueous solution of alcohol, having a pH of between about 5.5 to 6.5 and a molarity of about 0.02 to 0.08 based on said acid, said formaldehyde being present in a ratio of 2:1 to said acid, heating said solution to between about 60 to 100 C., immersing the keratin fibers in said solution for about one hour while maintaining said temperature, and drying said keratin fibers, whereby the dimensional stability and bacterial resistance are increased without changing the color of the keratin fibers.
  • a keratin fiber substrate comprising at least about 25% by weight of keratin fibers modified with the reaction product of 4,4-bis(4-hydroxy phenyl) pentanoic acid and an aldehyde selected from the class consisting of formaldehyde, acetaldehyde, benzaldehyde and propionaldehyde.
  • a keratin fiber substrate modified with the reaction product of 4,4-bis(4-hydroxy phenyl) pentanoic acid and formaldehyde.
  • a keratin fiber substrate modified with the reaction product of 4,4-bis(4-hydroxy phenyl) pentanoic acid and acetaldehyde.
  • a keratin fiber substrate modified with the reaction product of 4,4-bis(4-hydroxy phenyl) pentanoic acid and benzaldehyde.
  • a papermakers felt comprising a woven wool fiber base modified With the reaction product of 4,4-bis(4-hy droxy phenyl) pentanoic acid and formaldehyde.
  • a keratin fiber material modified with up to about 20% by Weight of the reaction product of 4,4-bis(4-hydroxy 'phenyl) pentanoic acid and formaldehyde.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US227540A 1962-10-01 1962-10-01 Papermaker's felt, woven fabrics and fibers of wool modified with an aldehyde - 4,4 - bis(4 - hydroxy phenyl) pentanoic acid reaction product and the production thereof Expired - Lifetime US3226179A (en)

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Application Number Priority Date Filing Date Title
US227540A US3226179A (en) 1962-10-01 1962-10-01 Papermaker's felt, woven fabrics and fibers of wool modified with an aldehyde - 4,4 - bis(4 - hydroxy phenyl) pentanoic acid reaction product and the production thereof
US245393A US3292992A (en) 1962-10-01 1962-12-18 Process for treating papermakers' felt and products obtained therefrom
GB31509/63A GB1029803A (en) 1962-10-01 1963-08-09 Treatment of proteinaceous material to improve the properties without substantially modifying the color
FR946031A FR1377382A (fr) 1962-10-01 1963-08-29 Procédé d'amélioration des propriétés de matières protéiques
NL297429D NL297429A (US06826419-20041130-M00005.png) 1962-10-01 1963-09-03
DE19631444074 DE1444074B1 (de) 1962-10-01 1963-09-06 Verfahren zur Verbesserung der Dimensionsstabilitaet unter gleichzeitiger Verbesserung der Gebrauchs- und Bakterienbestaendigkeit und chemischen Bestaendigkeit von Proteinmaterial oder solches enthaltendem synthetischem Material
SE9783/63A SE309959B (US06826419-20041130-M00005.png) 1962-10-01 1963-09-06
SE2372/67A SE309767B (US06826419-20041130-M00005.png) 1962-10-01 1967-02-21

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US227540A US3226179A (en) 1962-10-01 1962-10-01 Papermaker's felt, woven fabrics and fibers of wool modified with an aldehyde - 4,4 - bis(4 - hydroxy phenyl) pentanoic acid reaction product and the production thereof
US245393A US3292992A (en) 1962-10-01 1962-12-18 Process for treating papermakers' felt and products obtained therefrom

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4715931A (en) * 1987-03-24 1987-12-29 Betz Laboratories, Inc. Process for inhibiting aluminum hydroxide deposition in papermaking felts
WO2004011719A1 (en) * 2002-07-30 2004-02-05 Tamfelt Oyj Abp Fabric for paper machine
US7984567B2 (en) * 2008-10-07 2011-07-26 Christ Bill Bertakis Apparatus for cleaning simulated hair articles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7160867B2 (en) * 2003-05-16 2007-01-09 Isotechnika, Inc. Rapamycin carbohydrate derivatives

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1539517A (en) * 1921-08-27 1925-05-26 Basf Ag Process for tanning
US2512709A (en) * 1947-11-24 1950-06-27 Du Pont Chloral-dihydric phenol polymers
GB648854A (en) * 1947-09-05 1951-01-17 Lister & Company Ltd Improvements in or relating to the straightening of animal fibres, particularly in the form of furs and pile fabrics
US2676170A (en) * 1950-07-15 1954-04-20 Du Pont Water-soluble derivatives of unsulfonated lignin
US2837563A (en) * 1948-10-01 1958-06-03 Basf Ag Water soluble albumin-precipitating condensation products
US2907738A (en) * 1955-06-30 1959-10-06 Johnson & Son Inc S C Mixed resin acid esters of 4, 4-bis(4-hydroxyaryl) pentanoic acid

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB243317A (en) * 1924-11-20 1926-03-11 Robert Bach Improvements in the manufacture of hats
US2552129A (en) * 1946-05-11 1951-05-08 John R Evans & Company Tanning with a free aldehyde and a free polyhydric phenol mixture in a molecular ratio of at least 2 to 1
US2840445A (en) * 1954-06-09 1958-06-24 Koppers Co Inc Process of retaning mineral tanned leather with resorcinol-formaldehyde
BE541730A (US06826419-20041130-M00005.png) * 1954-10-01

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1539517A (en) * 1921-08-27 1925-05-26 Basf Ag Process for tanning
GB648854A (en) * 1947-09-05 1951-01-17 Lister & Company Ltd Improvements in or relating to the straightening of animal fibres, particularly in the form of furs and pile fabrics
US2512709A (en) * 1947-11-24 1950-06-27 Du Pont Chloral-dihydric phenol polymers
US2837563A (en) * 1948-10-01 1958-06-03 Basf Ag Water soluble albumin-precipitating condensation products
US2676170A (en) * 1950-07-15 1954-04-20 Du Pont Water-soluble derivatives of unsulfonated lignin
US2907738A (en) * 1955-06-30 1959-10-06 Johnson & Son Inc S C Mixed resin acid esters of 4, 4-bis(4-hydroxyaryl) pentanoic acid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4715931A (en) * 1987-03-24 1987-12-29 Betz Laboratories, Inc. Process for inhibiting aluminum hydroxide deposition in papermaking felts
WO2004011719A1 (en) * 2002-07-30 2004-02-05 Tamfelt Oyj Abp Fabric for paper machine
US7984567B2 (en) * 2008-10-07 2011-07-26 Christ Bill Bertakis Apparatus for cleaning simulated hair articles

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FR1377382A (fr) 1964-11-06
DE1444074B1 (de) 1970-04-09
SE309767B (US06826419-20041130-M00005.png) 1969-04-08
US3292992A (en) 1966-12-20
NL297429A (US06826419-20041130-M00005.png) 1965-11-10
GB1029803A (en) 1966-05-18
SE309959B (US06826419-20041130-M00005.png) 1969-04-14

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