US3366509A - Textile process and composition - Google Patents
Textile process and composition Download PDFInfo
- Publication number
- US3366509A US3366509A US450188A US45018865A US3366509A US 3366509 A US3366509 A US 3366509A US 450188 A US450188 A US 450188A US 45018865 A US45018865 A US 45018865A US 3366509 A US3366509 A US 3366509A
- Authority
- US
- United States
- Prior art keywords
- copolymer
- yarn
- acrylic acid
- weight ratio
- itaconic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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
- D06M15/21—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2971—Impregnation
Definitions
- ABSTRACT OF THE DISCLOSURE Polymeric material prepared by polymerizing itaconic acid with acrylic acid in a weight ratio of from about 0.5: 1.0 to about 2.0: 1.0 and having a Brookfield viscosity of from about 500 cps. to about 50,000 cps. in a 33% aqueous solution at 25 C. employed as a sizing agent for polyolefin yarn.
- This invention relates to an improved textile process and to the compositions produced thereby. More particularly, it is concerned with a new and improved method for sizing synthetic textile yarn, especially polyolefin yarn, and with the novel compositions produced by this treatment.
- the advantages offered by the use of the new polymeric sizing agents of this particular invention are truly manifest, since they now provide for the first time a new polyolefin warp size in addition to being useful as excellent sizing agents for nylon as well.
- sizing agents give good adhesion properties and hence, little shed, good protection during weaving, no gumming on the machine, stability in the size bath, and easy scourability as previously mentioned.
- they are also relatively easy to prepare and simple to handle in their operation and for this reason, they also find themselves to be economically attractive to the general user in this field.
- the two co-monomers of choice viz., itaconic acid and acrylic acid
- the two co-monomers of choice are heated together in the aforestated desired weight ratios in an aqueous solvent medium in the presence of a free-radical initiator at a temperature that is in the range of from between about 35 C. and C., until such time as said copolymerization reaction is substantially complete with respect to the formation of said polymer, i.e., until a copolymer product is achieved having a Brookfield viscosity of from about 500 cps. to about 50,000 cps. in 33% aqueous solution at room temperature.
- Suitable free-radical initiators for use in this reaction include potassium persulfate, ammonium persulfate, benzoyl peroxide, azobisisobutyronitrile, etc., or a redox system comprising persulfate-metabisulfite, with the more water-soluble agents being preferred.
- All these freeradical initiators are generally used at concentration levels ranging as low as from about 0.15 up to about 2.0 mole percent, based on the total weight of the comonomers employed.
- concentration of the latter two ingredients in solution is generally not critical, but it is preferred in practice to keep the combined itaconic-acrylic acid weight concentration in the 10-50% concentration range for the sake of convenience and economy.
- the desired copolymer may be recovered in solid form from the aqueous solution by means of precipitation therefrom with a non-solvent such as acetone, for example.
- a non-solvent such as acetone
- This step is then followed by filtration or decantation to remove the aqueous liquid from the polymer, which can then be subsequently dried to constant weight and further purified, if necessary, by additional treatment with aque' ous acetone in the usual manner.
- This material is then used to prepare the sizing solution, wherein the copolymer is dissolved in water to provide a copolymer solution strength of from about 1% up to about 20% by weight.
- the solution thus obtained is then used to size the polyolefin yarn or fiber by merely treating the latter material with said aqueous solution in the usual manner in accordance with the standard practice of the textile industry.
- the polyolefin yarn must be sized with at least about one part by weight, per parts by weight of the yarn,
- the polymeric sizing agent of this invention in order for completely effective and highly satisfactory results to be achieved.
- the latter value is not absolutely critical since some sizing effect is alway obtained below the lower limit hereinbefore stated.
- the polymeric sizing agent must always be one chosen from the group consisting of those copolymers which are prepared by polymerizing itaconic with acrylic acid in a weight ratio of from about 0.5 :1.0 to about 2.0210, respectively, as previously discussed, whereby a copolymer is produced having a Brookfield viscosity reading of from about 500 cps. to about 50,000 cps. when in 33% aqueous solution at 25 C.
- copolyrner formed by polymerizing itaconic acid with acrylic acid in a l.8:l.0 reaction weight ratio, respective ly, i.e., in equimolar amounts.
- This particular copolyrner which has a Brookfield viscosity reading in the neighborhood of 9S03,200 cps., has been found to be a most highly excellent polypropylene warp size on testing and is therefore, one of the most preferred member species of this invention for these particular purposes, as is also the copolymer of 1.0:l.0 reactant weight ratio. While the other copolymers of this invention work also equally as well, those remaining outside the scope of the aforestated viscosity range are just not at all effective from a practical standpoint when considered as sizing agents for the polyolefin yarns.
- the itaconic acid-acrylic acid copolymer so produced possesses the following characteristic physical properties in aqueous solution: Brookfield viscosity, #2 spindle, 30 rpm. at 25 C., 970 centipoise (cps.); specific (gfgiglity at 15/15 C., C., 1.154; n /C g, 0.64; n /C g,
- the solid polymer is then recovered from the aqueous solution by carefully pouring the latter into 15 times its volume of acetone, whereby the polymer slowly precipitates therefrom in the form of a gummy solid. After removal of the acetone liquid phase by decantation, the polymer is redissolved in water and reprecipitated again from acetone to obtain a white powder, which is then subsequently collected on a filter funnel by means of suction filtration and dried thereon to constant weight while under diminished pressure to afiord the pure product, viz., the itaconic-acrylic acid copolymer of 1.8210 reactant weight ratio.
- Example H The procedure described in Example I is then repeated to prepare other itaconic-acrylic acid copolymers in the reactant Weight ratio range of 1.6210 to 2021.0, respectively, by merely increasing or decreasing the amount of itaconic acid in each run as the case may be. For instance, 1008 g. of itaconic acid is used instead of 910 g. to prepare the 2.0: 1.0 reaction weight ratio copolyrner, whereas only 806.4 g. of the same said acid need be used to react with 504 g. of acrylic acid to prepare the 1.6:1.0 reactant weight ratio copolyrner.
- EXAMPLE III A polypropylene multifilament yarn of 210 denier, having 8 twists/inch, was threaded on a Calloway laboratory slasher machine, while a 7% aqueous solution of the itaconic-acrylic copolyrner prepared as described in Example I, viz., the copolyrner obtained by reacting itaconic acid with acrylic acid in a 1.8: 1.0 weight ratio, respectively (i.e., on an equimolar basis), was introduced into the size box of said slasher machine. The sizing was then conducted at a bath temperature of 120 F. (43-49" C.), and the squeeze rolls were adjusted to give a size add-on of 2.0%.
- the so-treated yarn was then subsequently tested on a Duplan testing machine to determine the abrasion resistance thus produced. It was found that adhesion of the size to the fiber was excellent and that a Duplan test result of cycles was obtained before all the filament ends became loose. This value was far superior to that obtained with unsized polypropylene (the control), where only a 10-cycle reading could be obtained. Further, the size on the yarn was easily removed by means of standard scouring treatments applied thereafter.
- EXAMPLE IV The sized polypropylene prepared as described in the above manner (where itaconic-acrylic acid copolymer of 1.8:1.0 reactant weight ratio is the sizing agent) was subjected to a warp shed test and compared at the same time in this respect with the polyethylene glycol type resins used in the trade for sizing polypropylene filter cloth. It was found that polypropylene yarn sized with the itaconicacrylic acid copolyrner at an add-on level of 2.03% gave a zero reading, i.e., no breaks, in the warp shed tests at 40 yards/fiber in comparison with a similar performance by the yarns sized with the aforementioned polyethylene oxide derivative at an add-on level of 10.5%. The shed which formed in the present instance was powdery, not gummy and was easily blown off the machine.
- Example V The procedure described in Example I is essentially followed on a larger scale except that 24.61 kg. of itaconic acid and 13.61 kg. of acrylic acid in 67.6 liters of deionized water are the reactants employed. This mixture is next heated to 48 C., at which point 514 g. of potassium persulfate in 8,875 ml. of water is added. The temperature is then adjusted to 50:1" C. and thereafter maintained at this point for 34 hours, with an additional amount (250 g.) of potassium persulfate having been added at the 20- hour mark. A bromine number analysis at the 27-hour mark indicated a 96% completeness of reaction.
- the itaconic-acrylic acid (1.8:1.0 reactant weight ratio) copolymer so obtained possesses the following characteristic physical properties: Brookfield viscosity, #2 spindle, 30 rpm. at 27 C., 3,170 centipoise;
- EXAMPLE VI A 3-twist/inch multifilament polypropylene yarn was sized in the manner of Example 111 except that the copolymer employed was that of Example V and the add-on level of said copolymer was now by weight of the fiber instead of the lower level previously used. Weaving tests performed on the treated material showed a 100% efficiency, i.e., no breaks, even after three days of weaving and this, despite the fact that no surfactant was required to obtain such highly satisfactory results. Although some shed was noticed on the reeds in the loom, this was not considered serious since it was not excessive and since it was a dry powder which could easily be blown off.
- EXAMPLE VIII In a 200-gallon stainless-steel stirred reactor vessel equipped with a water jacket for cooling and heating purposes as well as with an automatic stirrer, there is placed 176.8 lbs. of refined itaconic acid in 625.68 lbs. of deionized water. The stirrer is then started and the system is purged with nitrogen by displacing the air above the solution with said gas. The purged bath is then heated to 45 C., at which point 176.8 lbs. of glacial acrylic acid is added to the system. The temperature is next raised to 47 C. in order to facilitate homogeneity of the batch and then brought back to 42 C., at which point the catalyst is added, i.e., 1165 g.
- This particular itaconic acid-acrylic acid copolymer of 1:1 reactant weight ratio is found to possess the following characteristic properties in said 33.4% aqueous solution: Brookfield viscosity, #4 spindle, 30 r.p.m. at 25 C., 12,200 cps.; specific gravity at /15 C., 1. 88; n, 1.3904.
- the above copolymer solution of 33.4% total solids concentration strength is then filtered through a large Buchner funnel dressed with polypropylene cloth to remove dust particles and impurities, and the resulting aqueous filtrate is then subsequently diluted with sufiicient deionized water to afford a solution of 25.5 total solids copolymer concentration strength. This is done by simply charging 898 lbs. of the aqueous filtrate of 33.4% concentration strength with 278 lbs. of the de-ionized water with the aid of constant stirring. The resulting batch is next heated to 35 C. and stirred at that point for four hours.
- the copolymer After cooling to room temperature under a nitrogen atmosphere, it is subsequently filtered and the filtrate collected, i.e., packaged, in the same manner as before in the case of the 33.4% solution (total weight of 25.5% solution, 1084.4 lbs.).
- the copolymer is found to possess the following characteristic properties in this 25 .5 aqueous solution: Brookfield viscosity, #3 spindle, 30 rpm. at 25 C., 1570 cps; specific gravity at 15 15 C., 1.1190; n 1.3736.
- the actual copolymer is isolated in the same manner as that described in Example I for the 1.8:1.0 reactant weight ratio polymer, whereby acetone is employed as the anti-solvent of choice to precipitate the desired copolymer from aqueous solution. In this way, the pure itaconicacrylic acid copolymer of 1.0:1.0 reactant weight ratio is obtained in the form of a white powder.
- EXAMPLE X A warp was made with spun polypropylene 13/1 yarn (i.e., a yarn having 13 hanks per pound, which is also a single and not a Z-ply yarn).
- the warp was of standard construction, having 63 ends and 35 picks 'per inch, and being 12 inches wide and 64 yarns long.
- This particular warp was slashed in the following manner, viz., by mixing 6.5 lbs. of potato starch and 6.25 lbs. of itaconic acidacrylic acid copolymer of 1.0210 reactant weight ratio (in the form of the 25.5 aqueous solution prepared in Example VHI) together in the cold, then diluting the mix to five gallons with water, heating to F.
- Example XI The procedure described in Example X to size spun polypropylene yarn, using the itaconic-acrylic acid copolymer of 1.0:1.0 reactant weight ratio prepared in Example VIII, is repeated here with polyethylene spun yarn instead and equally satisfactory results are obtained.
- a polyolefin yarn sized with at least about one part by Weight, per 100 parts by weight of the yarn, of a copolymer of itaconic acid and acrylic acid in a weight ratio of from about 0.5 21.0 to about 2.0:1.0, said copolymer having a Brookfield viscosity of from about 500 cps. to about 50,000 cps. in a 33% aqueous solution at 25 C.
- polyolefin yarn as claimed in claim 1 wherein the polyolefin yarn is polyethylene sized with a copolymer of itaconic acid and acrylic acid prepared by polymerizing the latter two compounds together in an approximate weight ratio of from about 0.5:1.0 to about 2.0:1.0, respectively.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US450188A US3366509A (en) | 1964-05-25 | 1965-04-22 | Textile process and composition |
FR18373A FR1441831A (fr) | 1964-05-25 | 1965-05-25 | Perfectionnements aux compositions textiles et aux procédés pour leur établissement |
BE664443D BE664443A (de) | 1964-05-25 | 1965-05-25 | |
GB22240/65A GB1104416A (en) | 1964-05-25 | 1965-05-25 | Improvements in the sizing of polyolefin yarns |
DE19651469461 DE1469461A1 (de) | 1964-05-25 | 1965-05-25 | Verfahren zum Schlichten von Polyolefingarn |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37005864A | 1964-05-25 | 1964-05-25 | |
US450188A US3366509A (en) | 1964-05-25 | 1965-04-22 | Textile process and composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US3366509A true US3366509A (en) | 1968-01-30 |
Family
ID=27004795
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US450188A Expired - Lifetime US3366509A (en) | 1964-05-25 | 1965-04-22 | Textile process and composition |
Country Status (5)
Country | Link |
---|---|
US (1) | US3366509A (de) |
BE (1) | BE664443A (de) |
DE (1) | DE1469461A1 (de) |
FR (1) | FR1441831A (de) |
GB (1) | GB1104416A (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4485223A (en) * | 1981-10-29 | 1984-11-27 | Pfizer Inc. | (Meth)acrylic acid/itaconic acid copolymers, their preparation and use as antiscalants |
US4622370A (en) * | 1984-05-01 | 1986-11-11 | Diamond Shamrock Chemicals Company | Aqueous drilling fluids containing fluid loss additives |
US5032646A (en) * | 1981-10-29 | 1991-07-16 | Pfizer Inc. | (Meth)acrylic acid/itaconic acid copolymers, their preparation and use as antiscalants |
US5314943A (en) * | 1990-11-30 | 1994-05-24 | Rohm And Haax Company | Low viscosity high strength acid binder |
US20160068620A1 (en) * | 2013-03-15 | 2016-03-10 | Lubrizol Advanced Materials, Inc. | Itaconic Acid Polymers |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2544722B1 (fr) * | 1983-04-20 | 1985-07-05 | Coatex Sa | Agent hydrosoluble de complexation des cations metalliques compose de terpolymeres acryliques disposant d'un haut pouvoir complexant et d'un effet de seuil eleve |
US5180790A (en) * | 1983-04-20 | 1993-01-19 | Coatex S.A. | Water soluble complexing agent for metallic cations |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2789099A (en) * | 1953-09-04 | 1957-04-16 | Union Carbide & Carbon Corp | Polymerization of acrylic acid in aqueous solution |
US3055873A (en) * | 1960-07-27 | 1962-09-25 | Pfizer & Co C | Preparation of polyitaconic acid |
US3228791A (en) * | 1962-10-26 | 1966-01-11 | Nat Starch Chem Corp | Sized polyolefin yarn |
US3236685A (en) * | 1962-06-20 | 1966-02-22 | Eastman Kodak Co | Process for treating textile fibers and other shaped products with coatings |
-
1965
- 1965-04-22 US US450188A patent/US3366509A/en not_active Expired - Lifetime
- 1965-05-25 FR FR18373A patent/FR1441831A/fr not_active Expired
- 1965-05-25 GB GB22240/65A patent/GB1104416A/en not_active Expired
- 1965-05-25 DE DE19651469461 patent/DE1469461A1/de active Pending
- 1965-05-25 BE BE664443D patent/BE664443A/xx unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2789099A (en) * | 1953-09-04 | 1957-04-16 | Union Carbide & Carbon Corp | Polymerization of acrylic acid in aqueous solution |
US3055873A (en) * | 1960-07-27 | 1962-09-25 | Pfizer & Co C | Preparation of polyitaconic acid |
US3236685A (en) * | 1962-06-20 | 1966-02-22 | Eastman Kodak Co | Process for treating textile fibers and other shaped products with coatings |
US3228791A (en) * | 1962-10-26 | 1966-01-11 | Nat Starch Chem Corp | Sized polyolefin yarn |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4485223A (en) * | 1981-10-29 | 1984-11-27 | Pfizer Inc. | (Meth)acrylic acid/itaconic acid copolymers, their preparation and use as antiscalants |
US5032646A (en) * | 1981-10-29 | 1991-07-16 | Pfizer Inc. | (Meth)acrylic acid/itaconic acid copolymers, their preparation and use as antiscalants |
US4622370A (en) * | 1984-05-01 | 1986-11-11 | Diamond Shamrock Chemicals Company | Aqueous drilling fluids containing fluid loss additives |
US5314943A (en) * | 1990-11-30 | 1994-05-24 | Rohm And Haax Company | Low viscosity high strength acid binder |
US20160068620A1 (en) * | 2013-03-15 | 2016-03-10 | Lubrizol Advanced Materials, Inc. | Itaconic Acid Polymers |
Also Published As
Publication number | Publication date |
---|---|
FR1441831A (fr) | 1966-06-10 |
BE664443A (de) | 1965-11-25 |
DE1469461A1 (de) | 1969-01-02 |
GB1104416A (en) | 1968-02-28 |
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