US2981978A - Process of shrinking solid polymethylene terephthalate with halogenated methanes - Google Patents
Process of shrinking solid polymethylene terephthalate with halogenated methanes Download PDFInfo
- Publication number
- US2981978A US2981978A US531582A US53158255A US2981978A US 2981978 A US2981978 A US 2981978A US 531582 A US531582 A US 531582A US 53158255 A US53158255 A US 53158255A US 2981978 A US2981978 A US 2981978A
- Authority
- US
- United States
- Prior art keywords
- shrinking
- methylene chloride
- polymethylene terephthalate
- halogenated methanes
- partially halogenated
- 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
- 238000000034 method Methods 0.000 title claims description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims description 11
- -1 polymethylene terephthalate Polymers 0.000 title claims description 7
- 239000007787 solid Substances 0.000 title claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 229920000728 polyester Polymers 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 239000004744 fabric Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920008651 Crystalline Polyethylene terephthalate Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/04—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres having existing or potential cohesive properties, e.g. natural fibres, prestretched or fibrillated artificial fibres
- D04H1/06—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres having existing or potential cohesive properties, e.g. natural fibres, prestretched or fibrillated artificial fibres by treatment to produce shrinking, swelling, crimping or curling of fibres
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/04—Polyester fibers
Definitions
- polyesters of the aforementioned patent have been utilized for the production of many commercial products.
- several serious problems have arisen.
- One such is the difficulty in controlling the shrinkage of the structures. This problem is particularly acute in the manufacture of polyester felts and fabrics, since proper shrinkage of the felts and fabrics is necessary to impart satisfactory handle to the materials.
- This process comprises shrinking the structure by treating it with a normally liquid partially halogenated methane.
- the partially halogenated methane employed can be methylene chloride, chloroform, monochloromethane, chlorobromomethane, chloroiodomethane, tribromomethane, dibromomethane and the like. Because of their extremely fast action, ease of handling, and quick drying, the preferred agents are methylene chloride and chloroform.
- This shrinking treatment is ordinarily carried on by submerging the oriented crystalline polyester structure in a liquid bath containing the partially halogenated methane in a liquid phase.
- the treating bath can consist solely of one or more of the above described partially halogenated methanes.
- the bath can be an emulsion containing a partially halogenated methane liquid phase.
- the minimum amount of partially halogenated methane present in the emulsion treatment bath is not critical so long as there is a distinct liquid phase of partially halogenated "methane.
- an emulsion of methylene chloride in water can be used. Since methylene chloride is soluble in water in an amount equal to about 2% by weight at room temperature, a methylene chloride-water emulsion containing any amount in excess of about 2% by weight is satisfactory for practicing this invention at room temperature.
- the particular temperature employed in practicing the method of this invention is not critical. It can be carried out at all temperatures ordinarily used for synthetic textile treatment.
- Example 1 type batt is ideally suited for various air filtration uses.
- a second batt sample prepared as above was immersed in a bath of methylene chloride at room temperature. This second batt also shrunk gradually and evenly 44% areawise to yield a uniform felted product substantially free from wrinkles.
- a third sample was immersed in boiling water. This sample shrank immediately 44% in area, yielding a dense highly wrinkled product much inferior to the unwrinkled products treated with the partially halogenated alkanes.
- Example 11 Fabric samples made from- 2 /2 inch staple 3-denier per filament oriented crystalline polyethylene terephthalate fibers were treated for 5 minutes at C. in an emulsion of 10% by weight methylene chloride in water. This treatment was carried on under pressure to avoid excessive volatilization of the methylene chloride. After dyeing in accordance with conventional procedure, it was found that the thusly treated fabric samples exhibited a much improved handle, as compared to untreated dyed control samples. Furthermore, the treated samples had shrunk considerably.
- Example Ill Fabric samples were treated in accordance with the procedure of Example II, but using methylene bromide as the shrinking agent at atmospheric pressure. The same type of shrinkage and improved handle resulted.
- Example IV A series of tests similar to those set forth in Example I were performed but with the methylene chloride treatment being carried on at temperatures ranging from 25 C. to 80 C. All the treated samples shrunk substantially and exhibited greatly improved handle.
- Example V Another series of tests in accordance with the procedure of Example I was carried on but using a methylene chloride treating bath in place of the methylene chloride-water emulsion bath of Example I.
- the treated samples exhibited the same shrinkage and improved handle as the samples of Example I.
- X is halogen and each Y is selected from the group consisting of hydrogen and halogen, until the said structure shrinks.
- Theterm oriented crystalline polyester structures refers to structures comprising poly- 3.
- X 0 is chlorine.
- a process of improving a formed article formed from a high polymeric polyethylene terephthalate which comprises subjecting said formed article to stretching, and
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatment Of Fiber Materials (AREA)
Description
PROCESS OF SHRINKING SOLID POLYMETHYL- ENE TEREPHTHALATE WITH HALOGENATED METHANES This invention relates to a process for shrinking oriented crystalline polymeric structures such a fibers, filaments, films, fabrics, feltsand the like comprising a polyester of the type disclosed in U.S. Patent No. 2,465,319.
The polyesters of the aforementioned patent have been utilized for the production of many commercial products. In their production several serious problems have arisen. One such is the difficulty in controlling the shrinkage of the structures. This problem is particularly acute in the manufacture of polyester felts and fabrics, since proper shrinkage of the felts and fabrics is necessary to impart satisfactory handle to the materials.
Numerous treatments have been used to overcome these various problems. However, most of these treatments have not been completely acceptable for one or more reasons, such as excessive cost of either the reactants or the equipment required for the treatments.
We have discovered an improved process for shrinking solid oriented crystalline polyester structures. This process comprises shrinking the structure by treating it with a normally liquid partially halogenated methane. The partially halogenated methane employed can be methylene chloride, chloroform, monochloromethane, chlorobromomethane, chloroiodomethane, tribromomethane, dibromomethane and the like. Because of their extremely fast action, ease of handling, and quick drying, the preferred agents are methylene chloride and chloroform.
This shrinking treatment is ordinarily carried on by submerging the oriented crystalline polyester structure in a liquid bath containing the partially halogenated methane in a liquid phase. Thus the treating bath can consist solely of one or more of the above described partially halogenated methanes. Alternatively, the bath can be an emulsion containing a partially halogenated methane liquid phase.
The minimum amount of partially halogenated methane present in the emulsion treatment bath is not critical so long as there is a distinct liquid phase of partially halogenated "methane. By way of example, an emulsion of methylene chloride in water can be used. Since methylene chloride is soluble in water in an amount equal to about 2% by weight at room temperature, a methylene chloride-water emulsion containing any amount in excess of about 2% by weight is satisfactory for practicing this invention at room temperature.
The particular temperature employed in practicing the method of this invention is not critical. It can be carried out at all temperatures ordinarily used for synthetic textile treatment.
While this shrinking process is adapted to the treatment of the polyester materials of the above mentioned patent, namely the various polymeric polymethylene terephthalate materials, it is particularly efiective when applied to polyethylene terephthalate structures. Consequently, the following examples are given showing the practice of this invention in connection with polyethylene terephthalate. It is to be understood, however, that this method is un tfld vStates 2,981,978 Patented May 2, 1961 m equally applicable to the treating of the various other polyesters set forth in the patent.
In order that the invention can be better understood, the following examples in addition to those given above are set forth:
Example 1 type batt is ideally suited for various air filtration uses.
A second batt sample prepared as above was immersed in a bath of methylene chloride at room temperature. This second batt also shrunk gradually and evenly 44% areawise to yield a uniform felted product substantially free from wrinkles.
A third sample was immersed in boiling water. This sample shrank immediately 44% in area, yielding a dense highly wrinkled product much inferior to the unwrinkled products treated with the partially halogenated alkanes.
Example 11 Fabric samples made from- 2 /2 inch staple 3-denier per filament oriented crystalline polyethylene terephthalate fibers were treated for 5 minutes at C. in an emulsion of 10% by weight methylene chloride in water. This treatment was carried on under pressure to avoid excessive volatilization of the methylene chloride. After dyeing in accordance with conventional procedure, it was found that the thusly treated fabric samples exhibited a much improved handle, as compared to untreated dyed control samples. Furthermore, the treated samples had shrunk considerably.
Example Ill Fabric samples were treated in accordance with the procedure of Example II, but using methylene bromide as the shrinking agent at atmospheric pressure. The same type of shrinkage and improved handle resulted.
Example IV A series of tests similar to those set forth in Example I were performed but with the methylene chloride treatment being carried on at temperatures ranging from 25 C. to 80 C. All the treated samples shrunk substantially and exhibited greatly improved handle.
Example V Another series of tests in accordance with the procedure of Example I was carried on but using a methylene chloride treating bath in place of the methylene chloride-water emulsion bath of Example I. The treated samples exhibited the same shrinkage and improved handle as the samples of Example I.
Results similar to those of Examples I thru V are obtained by substituting for the shrinking agents of these examples various other partially halogenated methanes, such as those set forth above. Likewise, in place of the polyester fabrics and batts of these examples, fabrics of blends of polyester fibers with other fibers, such as wool, cotton or a synthetic fiber, can be used with similar results. Thus it is apparent that this process for shrinking oriented crystalline polyester structures is subject to numerous modifications all of which are within the scope of the invention.
wherein X is halogen and each Y is selected from the group consisting of hydrogen and halogen, until the said structure shrinks.
2. The method in accordance with claim 1 wherein said structure is a fabric.
g Theterm oriented crystalline polyester structures refers to structures comprising poly- 3. The method in accordance with claim 1 wherein X 0 is chlorine.
4. The method in accordance with claim 1 wherein said structure is a film.
5. The method in accordance with claim 1 wherein which comprises subjecting said formed article to stretching, and thereafter subjecting the stretched article to treatment for 15 seconds to 5 minutes with methylene chloride.
7. A process of improving a formed article formed from a high polymeric polyethylene terephthalate, which comprises subjecting said formed article to stretching, and
thereafter subjecting the stretched article to treatment for 15 seconds to 5 minutes with methylene chloride. References Cited inthefile of this patent UNITED STATES PATENTS 2,730,478 Morgan Jan. 10, 1956 2,734,001- Mecklenburgh Feb. 7,. 1956 2,856,638 Schulken Oct. 21, 1958 FOREIGN PATENTS 553,442 Great Britain May 21, 1943 555,490 Great Britain Aug. 25, 1943 578,079 Great Britain June 14, 1946
Claims (1)
1. THE METHOD OF SHRINKING A SOLID CRYSTALLINE ORIENTED HIGH POLYMERIC POLYMETHYLENE TEREPHTHALATE STRUCTURE COMPRISING CONTACTING IT WITH A NORMALLY LIQUID PARTIALLY HALOGENATED METHANE OF THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US531582A US2981978A (en) | 1955-08-30 | 1955-08-30 | Process of shrinking solid polymethylene terephthalate with halogenated methanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US531582A US2981978A (en) | 1955-08-30 | 1955-08-30 | Process of shrinking solid polymethylene terephthalate with halogenated methanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2981978A true US2981978A (en) | 1961-05-02 |
Family
ID=24118234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US531582A Expired - Lifetime US2981978A (en) | 1955-08-30 | 1955-08-30 | Process of shrinking solid polymethylene terephthalate with halogenated methanes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2981978A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094763A (en) * | 1961-05-10 | 1963-06-25 | Appleton Mills | Method of finishing papermakers' felt and the finished felt |
| US3228745A (en) * | 1961-01-10 | 1966-01-11 | Lehigh Valley Ind Inc | Process of shrinking nylon fabrics with mixtures of specific chemical shrinking agents |
| US3239586A (en) * | 1962-08-08 | 1966-03-08 | Du Pont | Process of molding polyester textile fabrics |
| US3920785A (en) * | 1969-11-13 | 1975-11-18 | Celanese Corp | Process for increasing the porosity of opencelled microporous film |
| US4356756A (en) * | 1981-04-03 | 1982-11-02 | Remo, Inc. | Method of forming a non-tunable head |
| US4416181A (en) * | 1981-04-03 | 1983-11-22 | Remo, Inc. | Pretuned head for drum or the like |
| US4421513A (en) * | 1979-01-08 | 1983-12-20 | Milliken Research Corporation | Process for producing fibrillated polyester |
| US4469001A (en) * | 1980-04-03 | 1984-09-04 | Remo, Inc. | Method of forming a non-tunable head |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB553442A (en) * | 1941-11-19 | 1943-05-21 | British Nylon Spinners Ltd | Improvements in and relating to the treatment of nylon fibres and fabrics |
| GB555490A (en) * | 1942-02-20 | 1943-08-25 | Ronald George Bartlett | Stiffened synthetic linear polyamide woven fabrics |
| GB578079A (en) * | 1941-07-29 | 1946-06-14 | John Rex Whinfield | Improvements relating to the manufacture of highly polymeric substances |
| US2730478A (en) * | 1954-03-05 | 1956-01-10 | Du Pont | Fibrous materials and processes for making same |
| US2734001A (en) * | 1956-02-07 | Setting and stiffening fabrics | ||
| US2856638A (en) * | 1954-07-20 | 1958-10-21 | Eastman Kodak Co | Process for the after-treatment of polymeric articles |
-
1955
- 1955-08-30 US US531582A patent/US2981978A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734001A (en) * | 1956-02-07 | Setting and stiffening fabrics | ||
| GB578079A (en) * | 1941-07-29 | 1946-06-14 | John Rex Whinfield | Improvements relating to the manufacture of highly polymeric substances |
| GB553442A (en) * | 1941-11-19 | 1943-05-21 | British Nylon Spinners Ltd | Improvements in and relating to the treatment of nylon fibres and fabrics |
| GB555490A (en) * | 1942-02-20 | 1943-08-25 | Ronald George Bartlett | Stiffened synthetic linear polyamide woven fabrics |
| US2730478A (en) * | 1954-03-05 | 1956-01-10 | Du Pont | Fibrous materials and processes for making same |
| US2856638A (en) * | 1954-07-20 | 1958-10-21 | Eastman Kodak Co | Process for the after-treatment of polymeric articles |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228745A (en) * | 1961-01-10 | 1966-01-11 | Lehigh Valley Ind Inc | Process of shrinking nylon fabrics with mixtures of specific chemical shrinking agents |
| US3094763A (en) * | 1961-05-10 | 1963-06-25 | Appleton Mills | Method of finishing papermakers' felt and the finished felt |
| US3239586A (en) * | 1962-08-08 | 1966-03-08 | Du Pont | Process of molding polyester textile fabrics |
| US3920785A (en) * | 1969-11-13 | 1975-11-18 | Celanese Corp | Process for increasing the porosity of opencelled microporous film |
| US4421513A (en) * | 1979-01-08 | 1983-12-20 | Milliken Research Corporation | Process for producing fibrillated polyester |
| US4469001A (en) * | 1980-04-03 | 1984-09-04 | Remo, Inc. | Method of forming a non-tunable head |
| US4356756A (en) * | 1981-04-03 | 1982-11-02 | Remo, Inc. | Method of forming a non-tunable head |
| US4416181A (en) * | 1981-04-03 | 1983-11-22 | Remo, Inc. | Pretuned head for drum or the like |
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