US3759858A - Acid modified poly vinyl acetate vinyl propionate textile - Google Patents

Acid modified poly vinyl acetate vinyl propionate textile Download PDF

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US3759858A
US3759858A US3759858DA US3759858A US 3759858 A US3759858 A US 3759858A US 3759858D A US3759858D A US 3759858DA US 3759858 A US3759858 A US 3759858A
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size
percent
textile
latex
interpolymer
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A Corey
D Donermeyer
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Monsanto Co
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Monsanto Co
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    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2402—Coating or impregnation specified as a size

Definitions

  • the present invention relates to textile sizes. More particularly it relates to acid-modified poly(vinyl acetatevinyl propionate) textile sizes and to textiles, especially polyester textiles sized with these materials.
  • yarn is sized with an aqueous solution of a water soluble material such as a copolymer of vinyl acetate and a carboxylic acid, woven into cloth on a conventional loom with a mechanical shuttle and then the size is removed in a water bath. While these sizes have been adequate for natural textile fibers and for many of the synthetic textile fibers, they exhibit poor adhesion to synthetic fibers, particularly to polyester fibers which are enjoying increasing use in broadwoven textiles. Interpolymers of vinyl acetate and maleates have better adhesion to polyester but insufficient to prevent shedding from the yarn, leaving it unprotected from the destructive forces of the loom.
  • a water soluble material such as a copolymer of vinyl acetate and a carboxylic acid
  • Acrylate sizes have good adhesion to polyester but lack the strength to hold the monofilaments together sufficiently to withstand the disruptive forces of the loom. This weakness may be overcome in an unsatisfactory fashion by heavier coatings of size but costs rise because of the heavier consumption of size and more importantly, because of frequent interruptions to repair breaks of the wrap caused by deposition and accumulation of size on the heddles an reeds of the loom.
  • Other sizes such as poly(vinyl alcohols), styrene maleic anhydride copolymers, poly- (acrylic acids) and gelatin are extremely poor in adhesion to polyester.
  • the textile sizes of the present invention have excellent solubility characteristics, film properties and adhesion to filament acetate, filament rayon and filament nylon and especially to filament and texturized polyester. Moreover, these sizes are easily removed from sized yarns or the resulting fabric using organic solvents, water or aqueous solutions of inorganic or organic monovalent bases.
  • the sizes of the present invention are prepared from latices obtained by interpolymerizing vinyl acetate, vinyl propionate and a variety of unsaturated organic carboxylic compounds containing from 3 to 9 carbon atoms and having at least one carboxyl group.
  • carboxylic acids examples include the unsaturated organic monocarboxylic acids, as for example acrylic acid, methacrylic acid, crotonic acid and isocrotonic acid.
  • unsaturated carboxylic acids include partial esters of unsaturated polybasic carboxylic acids, for example, the half esters of maleic acid, fumaric acid, citraconic acid and itaconic acid in which the alkyl group contains from 1 to 4 carbon atoms, such as methyl, ethyl, propyl and butyl maleates. Mixtures of these acids may be used in the preparation of the interpolymer latices.
  • the polymerization charge comprises from 50 to 92 percent by weight of vinyl acetate, from 5 to 40 percent by weight of vinyl propionate and from 3 to 10 percent by weight of ethylenically unsaturated carboxylic acid, based on the total weight of the monomers. More preferably, the polymerization charge comprises from 69 to 86 percent of vinyl acetate, from 10 to 25 percent of vinyl propionate and from 4 to 6 percent of ethylenically unsaturated carboxylic acid.
  • the upper limit of acid is set by latex stability; the lower limit by polymer solubility in aqueous base.
  • the monomers are polymerized using latex polymerization methods at a temperature in the range of from 40 to 60 C. and preferably at a temperature in the range of from 40 to 45 C. At temperatures below about 40 C. the polymerization rate is too slow and the reaction mass tends to coagulate. At polymerization temperatures above 60 C. the product is of low molecular weight and lacks the tensile strength and elongation required in sizes.
  • the interpolymerization is carried out using a surfactant which comprises a phosphate ester of an alkyl phenol-ethylene oxide condensate wherein the alkyl group contains from 7 to 11 carbon atoms.
  • a surfactant which comprises a phosphate ester of an alkyl phenol-ethylene oxide condensate wherein the alkyl group contains from 7 to 11 carbon atoms.
  • a surfactant which comprises a phosphate ester of an alkyl phenol-ethylene oxide condensate wherein the alkyl group contains from 7 to 11 carbon atoms.
  • PEOPEO phosphate esters of tertiary octyl phenol-ethylene oxide condensates
  • PENPEO nonyl phenolethylene oxide condensates
  • These preferred surfactants are available commercially as Triton XQS surfactants (Rohm & Haas Company) and GAFAC surfactants (General Aniline & Film Company), respectively.
  • the interpolymerization of the monomers is carried out using an anionic co-surfactant in combination with the phosphate esters of an alkyl phenolethylene oxide condensate.
  • the use of the co-surfactants reduces the amount of coagulum in the resulting latex and provides a better product.
  • the preferred co-surfactants used in the present invention include alkyl sulfonates such as sodium dodecyl benzene sulfonate; fatty alcohol sulfates such as sodium lauryl sulfate; dialkyl sulfosuccinates such as sodium dihexyl sulfosuccinate; etc.
  • the amount of co-surfactant used is in the range of 0.1 to 0.4 percent by weight and more preferably 0.20 to 0.30 percent by weight based on the total weight of the latex.
  • Suitable oxidizing components for the system are the inorganic peracid salts such as ammonium, potassium and sodium persulfates, perborates, and hydrogen peroxide.
  • Preferred, however, are the oil soluble organic hydroperoxides such as t-butyl hydroperoxide, cumene hydroperoxide, p-menthane hydroperoxide, etc. and esters of the t-butyl perbenzoate type.
  • the useful reducing components include compounds like the sulfites, bisulfites, hydrosulfites and thiosulfites; ethyl and other alkyl sulfites; the sulfoxylates, such as sodium formaldehyde sulfoxylate; and the like.
  • initiator systems based on t-butyl hydroperoxide and sodium formaldehyde sulfoxylate; and redox combinations such as mixtures of hydrogen peroxide and an iron salt, hydrogen peroxide and zinc formaldehyde sulfoxylate or other similar reducing agent; hydrogen peroxide and a titanous salt; potassium persulfate and sodium bisulfite and a bromate mixed with a bisulfite.
  • equimolar amounts of initiator system components is generally preferred although the amount of each component as well as the total amount of catalyst used depends on the type of component used as well as on other polymerization conditions and may range between .02 and 0.2 percent by weight of the total polymerization system, the preferred range being 0.03 to 0.10 percent for the oxidizing component and 0.04 to 0.1 for the reducing component.
  • the solids contents of the latices can be varied over a wide range.
  • the preferred latices having a solids content in the range of from to 65 percent by weight and more preferably from 35 to 55 percent by weight, based on the total Weight of the latex.
  • a conventional base such as ammonium hydroxide or sodium hydroxide is used to buffer the latex to a pH in the range of 4.0 to 6.0.
  • the textile size solution may be prepared from the latex in several ways.
  • an aqueous solution of base is mixed with the latex to dissolve the interpolymer by formation of the water soluble interpolymer carboxylate.
  • Suitable bases include the hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals such as sodium hydroxide, sodium carbonate and sodium bicarbonate; ammonia, organic bases such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, morpholine, etc.
  • the preferred base in the preparation of a loom finish size is ammonium hydroxide since it contributes to good adhesion and resistance to water, water spotting and dry cleaning.
  • the preferred base in the preparation of removable warp yarn size is sodium carbonate since it contributes to rapid solution of the interpolymer, good adhesion of the interpolymer size especiall to polyester yarn and rapid removability of the size.
  • a particular advantage of an interpolymer latex is that the fine size of the interpolymer particles allows rapid solubility of the interpolymer in aqueous base to form the size solution.
  • Another method for preparation of the textile size solution comprises the recovery of the interpolymer from the latex by conventional means and solution of the interpolymer in an organic solvent.
  • the size is then applied to the textile yarn as an organic solution and may be removed from the woven goods with aqueous base or organic solvent.
  • Preferred organic solvents for preparation of size solutions and removal of size are alcohols, ketones, esters and aromatic solvents.
  • chlorinated aliphatic hydrocarbons such as methylene chloride, methylene bromide, chloroform, bromoform, ethylene dichloride, ethylene dibromide, ethylidene chloride, ethylidene bromide, s-tetrachloroethane, hexachloroethane, s-dichloroethylene, 1,1,1 trichloroethane, 1,1,2 trichloroethane, trichloroethylene, trimethylene bromide, trichlorobromoethane, trichloromethane, 1,2,3-trichloropropane, 1,1,2-trichloropropane, trifluoro-l,1,2-tribromoethane, trifluoro-l,1,2-trichloroethane, 2,2 dichloro-l-bro
  • Example 1 A latex is prepared in conventional latex polymerization equipment. The following charge is used:
  • the resulting latex has a total solids of 35 percent, a pH of 5.0 and a Brookfield viscosity of 12 cps.
  • the interpolymer has a specific viscosity of 2.44 in dimethyl sulfoxide at a concentration of l g. per ml.
  • Other properties of the latex are tabulated in Table I below.
  • Examples 2 to 5 The following Examples 2 to 5 are set forth to illustrate variations in the latex polymerization of the present invention. In each case the general procedures of Example 1 are followed except for the noted changes. Polymerization temperatures are maintained in the range from 41 to 45 C. The resulting latices have solids contents of 35 percent by weight and Brookfield viscosities in the range from 10 to 50 cps. at 25 C. The examples are tabulated in Table I.
  • Tensile strength and elongation are measured according to ASTM Method D-882-67 on interpolymer neutralized with sodium carbonate, after conditioning at 65 percent relative humidity.
  • Adhesion values are the loads in pounds required to break /2 x inch polyester lap joints adhered with 0.15 mil film of interpolymer. Experience has shown that an adhesion value of at least 30 pounds is required for satisfactory size performance with filament polyester on a commercial machine.
  • the vinyl propionate level is varied between 0 and 30 percent. Interpolation of the data in Table I indicates that adhesion values would be unsatisfactory with interpolymers containing less than percent vinyl propionate. On the other hand, high concentrations of vinyl propionate in the interpolymer contribute to coagulation of the latex and to low molecular weight, low cohesive strength and tackiness of the polymeric size.
  • Examples 6 to 10 The following examples are set forth to illustrate the use of various acids in the preparation of the interpolymer latices.
  • the latices are prepared by the procedure described in Example 1.
  • Composition data for the interpolymers are presented in Table II. In every case a satisfactory latex and textile size is obtained.
  • Example 11 to 14 are set forth as control examples to illustrate the effect of polymerization temperature on the physical properties of the resulting latex.
  • Example 1 In each example the general procedure of Example 1 is repeated while the polymerization temperature is varied. The specific viscosity of the resulting polymer is then measured. The results are tabulated in Table III below.
  • the latices prepared in Examples 1 to 5 are tested in order to determine their suitability as yarn sizes in conventional weaving processes.
  • the sizes are prepared by dissolving the latex in a basic solution such as aqueous sodium carbonate, aqueous sodium hydroxide or aqueous ammonia.
  • Solubilityall of the latices in question are soluble in aqueous bases such as aqueous sodium carbonate to provide sizing solutions.
  • Sizing solutionsprepared from the latices of Examples 1 to 5 have Brookfield viscosities in the range of from 1 to 500 centipoises at 1 to 25 percent solids allowing ease of application to the yarn.
  • Adhesion-the latices of Examples 1 and 3 to have been tested and are found to have good adhesion to the following yarns-filaments, polyester, acetate rayon and nylon; texturized polyester; spun polyester, rayon, acetate and nylon.
  • Solubility in mild alkali-dried films of the latices in question are readily soluble in trisodium phosphate-surfactant solutions which indicate that the size is easily removed from the woven fabric.
  • Solubility in organic solvent-size solutions of interpolymer latex in aqueous ammonia are applied to yarn and dried.
  • the dried films are readily soluble in chlorinated hydrocarbons.
  • Size efiiciency- is a measure of the amount of size add-on required in a given operation.
  • the add-on is the amount of size that must be applied to the yarn in order to permit it to be woven on a loom. In general, the less size add-on required, the more eflicient the size. Sizes prepared from the latices of the present invention have high efiiciency as is indicated by the following Examples 15 and 16.
  • Polyester yarnfilament polyester yarn is understood to mean rigid uncrimped yarn. Textured polyester yarn is understood to mean drawn and crimped yarn.
  • Example 15 Filament polyester size.A 12 percent size solution is prepared by dissolving 2.9 pounds of sodium carbonate in 30 gallons of water, heating to 120 F. adding pounds of a latex similiar to Example 1 containing 36 weight percent of an interpolymer of vinyl acetate (70 parts), vinyl propionate (25 parts) and acrylic acid (5 parts). The solution is made up to 50 gallons with water. The resin dissolves rapidly at 130-140 F. The viscosity of the solution is 45 cps. at 25 C.
  • This sizing solution is applied at 130 F. to a 70 denier, 34 filament 5 turn per inch dull Type 57 Dacron filament polyester on a commercial seven can slasher, using a wet split section at 40 y.p.m., for a size add-on of 4.0 percent. Drying can temperatures are 300/ 220/ 220/220/220/ 190/ 200 F. The split is very easy.
  • the sized warp yarn is entered into a conventional Draper loom, weaving at 172 picks per minute.
  • First quality fabric is Woven at high efliciency.
  • the fabric is desized in a conventional process by scouring in an aqueous solution of trisodium phosphate and wetting agent.
  • Example 16 Texturized polyester size.A 6 percent size solution is prepared by dissolving 1.8 pounds of sodium carbonate in 30 gallons of water, heating to F., adding 70 pounds of a latex similar to Example 1, containing 36 weight percent of an interpolymer of vinyl acetate (70 parts), vinyl propionate (25 parts) and acrylic acid (5 parts). The resin dissolves rapidly at F. The solution is 7 brought to a final volume of 50 gallons. The viscosity of the solution is 7.5 cps. at 25 C.
  • This size solution is applied at 120 F. to a 150 denier 34 filament 1 turn texturized Dacron polyester on a commercial seven can slasher at 20 y.p.m.
  • a wet split was employed, and the warp split easily, with no ends out. There was no can sticking, or skinning. A size add-on of 3.0 percent was obtained.
  • the sized warp yarn was woven on a conventional loom. A high weaving efiiciency was obtained and the woven goods were of first quality.
  • the fabric was desized in a conventional process by scouring in a bath containing an aqueous solution of tri-sodium phosphate and nonionic wetting agent.
  • Sizes which are obtained from polymers prepared by the process of the present invention are compared to commercially available textile sizes.
  • the sizes in the form of the sodium salt are cast as films, dried and tested at 65 percent relative humidity for tensile strength, elongation and toughness.
  • the toughness value is the product of tensile strength and elongation.
  • Polyester lap jointsfl x A inch containing 0.15 mil thickness of interpolymer are tested for adhesion. The results of the comparison are set forth below.
  • the sized warp yarn is woven on a conventional loom. Size is removed from the woven goods by extraction with 1,1,1-trichloroethylene.
  • the sizes of the present invention may be formulated with lubricants, defoamers, humectants, plasticizers, softening agents and other adjuncts without departing from the scope of the invention.
  • a textile size which comprises an aqueous base solution of an interpolymerization product consisting essentially of from 50 to 92 percent by weight of vinyl acetate, from 5 to 40' percent by weight of vinyl propionate and from 3 to 10 percent by weight of an ethylenically unsaturated carboxylic acid selected from the group consisting of acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid and monoalkyl esters of maleic acid, fumaric acid, citraconic acid and itaconic acid in which the alkyl group contains from 1-4 carbon atoms, wherein the percent by Weight is based on the total weight of the monomers.
  • Example 17 A latex composition is prepared as in Example 1. The resulting latex is dissolved in aqueous ammonia to give a 5.0 percent solution of interpolymer having a pH of 9.0. The sizing solution is applied to 150 denier, 41 monofilament, low twist bright acetate yarn. The sized warp yarn is woven on a conventional loom. The size adheres well to the woven fabric and shows excellent resistance to water, water spotting and dry cleaning.
  • Example 18 A latex composition is prepared as in Example 1 and coagulated by addition of acetone. The interpolymer is recovered and dried. It is then dissolved in trichloroethylene to give a 5.0 percent solution. The solution is used to size filament nylon yarn.
  • Example 19 A latex composition is prepared as in Example 1. The resulting latex is dissolved in aqueous ammonia to give a 5.0 percent solution of interpolymer having a pH of 9.0. The solution is used to size filament polyester yarn.
  • amount of vinyl propionate is in the range from 10 to 25 percent and the amount of ethylenically unsaturated carboxylic acid containing from 3 to 9 carbon atoms is in the range from 4 to 7 percent by weight.
  • a textile size as in claim 1 wherein the ethylenically unsaturated carboxylic acid is selected from the group consisting of acrylic acid, crotonic acid, isocrotonic acid, monomethyl maleate and monomethyl fumarate.
  • aqueous base is an aqueous solution of a base selected from the group consisting of the hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals; ammonia; methylamine dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine and morpholine.
  • a textile size which comprises an aqueous base solution of a latex interpolymerization product consisting essentially of from 50 to 92 percent by Weight of vinyl acetate, from 5 to 40 percent by weight of vinyl propionate and from 3 to 10 percent by weight of an ethylenically unsaturated carboxylic acid selected from the group consisting of acrylic acid, crotonic acid, isocrotonic acid, monomethyl maleate and monomethyl fumarate, wherein the percent by weight is based on the total Weight of the monomers; wherein the interpolymer in dimethyl sulfox- 9 ide at a concentration of 1 gram per 100ml. has a specific viscosity in the range of from 1.3 to 10 at 25 C.; and wherein the size contains from 1 to 25 percent by weight of interpolymer based on the total weight of the aqueous solution.
  • a latex interpolymerization product consisting essentially of from 50 to 92 percent by Weight of vinyl acetate, from 5 to 40 percent by weight of
  • aqueous base is an aqueous solution of a base selected from the group consisting of the hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals; ammonia; methylamine climethylamine, trimethylamine, ethylamine, diethylamine, triethylamine and morpholine.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US3759858D 1971-10-04 1971-10-04 Acid modified poly vinyl acetate vinyl propionate textile Expired - Lifetime US3759858A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US18644171A 1971-10-04 1971-10-04
US36390373 US3860553A (en) 1971-10-04 1973-05-25 Acid-modified poly(vinyl acetate-vinyl propionate) textile sizes
US53024174 US3922461A (en) 1971-10-04 1974-12-06 Acid-modified poly(vinyl acetate-vinyl propionate) textile sizes

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US36390373 Expired - Lifetime US3860553A (en) 1971-10-04 1973-05-25 Acid-modified poly(vinyl acetate-vinyl propionate) textile sizes
US53024174 Expired - Lifetime US3922461A (en) 1971-10-04 1974-12-06 Acid-modified poly(vinyl acetate-vinyl propionate) textile sizes

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US53024174 Expired - Lifetime US3922461A (en) 1971-10-04 1974-12-06 Acid-modified poly(vinyl acetate-vinyl propionate) textile sizes

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CA (1) CA977086A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE2248504A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR2155995B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3919449A (en) * 1973-10-15 1975-11-11 Monsanto Co Acid-modified poly(vinyl acetate) textile sizes
US4129711A (en) * 1965-03-03 1978-12-12 L'oreal Polymers comprising vinyl esters-crotonic acid
US4258104A (en) * 1979-04-27 1981-03-24 The Dow Chemical Company Aqueous polymeric dispersions, paper coating compositions and coated paper articles made therewith
US5082896A (en) * 1989-01-17 1992-01-21 Milliken Research Corporation Polymeric materials useful for sizing synthetic yarns to be used in water jet weaving

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2543815C3 (de) * 1975-10-01 1980-08-21 Basf Ag, 6700 Ludwigshafen Verfahren zum Entschlichten von Geweben
US4480080A (en) * 1983-01-31 1984-10-30 Eastman Kodak Company Vinyl-ester polymeric timing layer for color transfer assemblages

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2855387A (en) * 1954-12-20 1958-10-07 Monsanto Chemicals Terpolymer of maleic anhydride, vinyl acetate and alkyl acrylate
US3003987A (en) * 1957-11-14 1961-10-10 Alco Oil & Chemical Corp Copolymer of acrylic acid ester, method of making, and use of said polymer to coat textile fabrics
GB1123829A (en) * 1964-12-01 1968-08-14 Minnesota Mining & Mfg Fluorine containing copolymers
US3455887A (en) * 1966-06-21 1969-07-15 Celanese Corp Copolymers of vinyl esters of lower alkanoic acid,vinyl esters of tertiary alkanoic and lower alkyl methacrylates
US3598641A (en) * 1968-11-29 1971-08-10 Klopman Mills Inc Process for improving the oil release and anti-static properties of a textile and the resulting product
US3694257A (en) * 1970-07-20 1972-09-26 Emery Industries Inc Polyester compositions and their use as textile assistants
US3716547A (en) * 1970-12-16 1973-02-13 Monsanto Co Process for the preparation of a poly(vinyl acetate-dialkyl maleaee-acrylic acid) textile sizes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129711A (en) * 1965-03-03 1978-12-12 L'oreal Polymers comprising vinyl esters-crotonic acid
US3919449A (en) * 1973-10-15 1975-11-11 Monsanto Co Acid-modified poly(vinyl acetate) textile sizes
US4258104A (en) * 1979-04-27 1981-03-24 The Dow Chemical Company Aqueous polymeric dispersions, paper coating compositions and coated paper articles made therewith
US5082896A (en) * 1989-01-17 1992-01-21 Milliken Research Corporation Polymeric materials useful for sizing synthetic yarns to be used in water jet weaving

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US3922461A (en) 1975-11-25
CA977086A (en) 1975-10-28
US3860553A (en) 1975-01-14
FR2155995A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-05-25
GB1378719A (en) 1974-12-27
DE2248504A1 (de) 1973-04-12

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