US3335093A - Dry cleaning process and composition - Google Patents
Dry cleaning process and composition Download PDFInfo
- Publication number
- US3335093A US3335093A US431205A US43120565A US3335093A US 3335093 A US3335093 A US 3335093A US 431205 A US431205 A US 431205A US 43120565 A US43120565 A US 43120565A US 3335093 A US3335093 A US 3335093A
- Authority
- US
- United States
- Prior art keywords
- dry cleaning
- present
- solvent
- swatches
- cleaned
- 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
- 238000005108 dry cleaning Methods 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title description 9
- 239000002904 solvent Substances 0.000 claims description 42
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 16
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 10
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004140 cleaning Methods 0.000 claims description 7
- 230000008021 deposition Effects 0.000 claims description 6
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002657 fibrous material Substances 0.000 claims description 5
- 150000001455 metallic ions Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 8
- 125000005594 diketone group Chemical group 0.000 description 8
- 229910021645 metal ion Inorganic materials 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 7
- 238000000151 deposition Methods 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- -1 wool Polymers 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
Definitions
- deposition of polyvalent metal ions from a solvent system onto fibrous materials being cleaned therein is inhibited by addition of minor amounts of a lower alkanedione or cycloalkanedione to the solvent system employed in the dry cleaning process. It is believed that this dione additive, which is soluble in the solvent system in the amounts used to practice the present invention, reacts with polyvalent metal ions present to polyvalent metal ions onto the material.
- the tendency of polyvalent metal ions to deposit on materials from the contacting dry cleaning solvent system is also demon- EXAMPLE 1 materials cleaned therein and that such deposits adversely effect the brightness Of the cleaned materials, experiments" were conducted to determine quantitative eflects of this unexpected phenomenon. Investigation revealed that the polyvalent metal ion deposit is in most instances, especially ;mar ked where moisture is present in the material. Moisto wet area deposition with subsequent capillary action.
- a quantity of from about 0.1 to 3 parts by weight of a lower alkanedione or a cycloalkanedione is added to 100 parts by weight of a dry cleaning solvent system to form a new composition of the present invention.
- This new composition is utilized to inhibit the previously described deposition of metallic impurities on fibrous materials during dry cleaning operations.
- the term lower alkanedione is used herein to designate an alkanedione containing from 1 to 6 carbon atoms, inclusive.
- cycloalkanedione as used herein includes cycloalkanediones having one or more alkyl substituents, which substituents contain from 1 to 4 carbon atoms, inclusive.
- These new compositions of the present invention may also be employed for purposes, other than usual dry cleaning procedures, where solvent systems are utilized. Examples of such uses include water repellant formulations, spotting agent, moth proofing and static eliminator systems and sizing solutions.
- lower alkanediones and cycloalkanediones employed in practice of the present invention include acetylacetone, 2,3-butanedione, 2,4-pen-tanedione, 2,5-hexanedione and 5,5-dimethyl-1,3-cyclohexanedione.
- EXAMPLE 3 A series of four glass containers holding 100 ml. quantities of a fresh solvent system and either cotton or spun acetate cloth samples was prepared.
- a commercially available solvent system widely used in coin-operated dry cleaning machines and containing small amounts of a petroleum sulfonate base detergent, was employed.
- a quantity of analytical reagent grade zinc, magnesium, iron and copper (0.2 gram each) was added to each glass container.
- the cotton swatches EXAMPLE 4 In the manner of the preceding experiment, a quantity of galvanized metal was employed in place of the Zn, Cu, Fe and Mg used above. Table III, below, shows the reflectance readings of cotton swatches, after various time periods, agitated in solvent systems with and without acetylacetone present. The initial reflectance of the cotton swatches, before treatment, was 75 units.
- Example 5 In this example the procedure of Example 3 was employed with the following exceptions; no iron was present, agitation time was 24 hours after which reflectance was measured, the solvent system employed was perchloroethylene and the diketones used in place of acetylacetone are as indicated in Table IV, below. Cotton swatches were used.
- a quantity of from about .01 to 3 parts by weight of a lower alkanedione or cycloalkanedione is dissolved in parts by weight of a dry cleaning solvent system to provide a new composition of the present invention.
- This solvent system comprises essentially a halogenated organic dry cleaning solvent base well known to the art.
- other additives such as soaps or detergents, water, brighteners, anti-static agents, etc. While these relatively small amounts of additives have no marked effect on the formation of the diketone-metal complexes, each plays a role in improving or providing other desirable features in a dry cleaning process.
- compositions of the present invention which consist essentially of a major amount of dry cleaning solvent and a minor amount of vent contains an agent which prevents the deposition of metallic ions upon the material being cleaned, said agent being a diketone selected from the group consisting of acetylacetone, 2,3-butanedione, 2,4-pentanedione, 2,5-hexanedione, and 5,5-dimethyl-1,3-cycloheX- anedione, said agent being present in an amount of from 0.01 to 3 weight percent.
- halogenated dry cleaning solvent is perchloroethylene containing a petroleum sulfonate base dry cleaning detergent.
- halogenated dry cleaning solvent is perchloroethylene containing a phosphate base dry cleaning detergent.
- a chlorinated hydrocarbon dry cleaning solvent containing from about 0.01 to 3 weight percent of a diketone selected from the group consisting of acetylacetone, 2,3-butanedione, 2,4-pentanedione, 2,5-hexanedione and 5,5-dimethyl-1,3-cyclohexanedione.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US431205A US3335093A (en) | 1965-02-08 | 1965-02-08 | Dry cleaning process and composition |
| BE700247D BE700247A (enrdf_load_stackoverflow) | 1965-02-08 | 1967-06-21 | |
| DED53467A DE1286252B (de) | 1965-02-08 | 1967-06-28 | Trockenreinigungsverfahren |
| GB29887/67A GB1150837A (en) | 1965-02-08 | 1967-06-28 | Dry Cleaning Process and Composition |
| NL6709211A NL6709211A (enrdf_load_stackoverflow) | 1965-02-08 | 1967-07-03 | |
| FR112893A FR1536343A (fr) | 1965-02-08 | 1967-07-03 | Procédé de nettoyage de matières textiles |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US431205A US3335093A (en) | 1965-02-08 | 1965-02-08 | Dry cleaning process and composition |
| IT3757567 | 1967-06-16 | ||
| GB29887/67A GB1150837A (en) | 1965-02-08 | 1967-06-28 | Dry Cleaning Process and Composition |
| NL6709211A NL6709211A (enrdf_load_stackoverflow) | 1965-02-08 | 1967-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3335093A true US3335093A (en) | 1967-08-08 |
Family
ID=27448773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US431205A Expired - Lifetime US3335093A (en) | 1965-02-08 | 1965-02-08 | Dry cleaning process and composition |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3335093A (enrdf_load_stackoverflow) |
| BE (1) | BE700247A (enrdf_load_stackoverflow) |
| GB (1) | GB1150837A (enrdf_load_stackoverflow) |
| NL (1) | NL6709211A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3546305A (en) * | 1967-12-01 | 1970-12-08 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
| US20080274935A1 (en) * | 2007-05-01 | 2008-11-06 | Enviro Tech International, Inc. | Detergent Composition for Halogenated Dry Cleaning Solvents |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1911289A (en) * | 1932-02-04 | 1933-05-30 | Emery Industries Inc | Method of cleaning fabrics |
| US2388962A (en) * | 1938-01-24 | 1945-11-13 | Allied Chem & Dye Corp | Dry cleaning composition |
| US2476554A (en) * | 1941-03-20 | 1949-07-19 | Continental Oil Co | Method of inhibiting deterioration of organic compounds |
| US2517895A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
| US3117152A (en) * | 1960-05-10 | 1964-01-07 | Stamford Chemical Ind Inc | Substantially neutral magnesium salt of a phosphoric acid ester of oxethylated nonylphenol |
-
1965
- 1965-02-08 US US431205A patent/US3335093A/en not_active Expired - Lifetime
-
1967
- 1967-06-21 BE BE700247D patent/BE700247A/xx unknown
- 1967-06-28 GB GB29887/67A patent/GB1150837A/en not_active Expired
- 1967-07-03 NL NL6709211A patent/NL6709211A/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1911289A (en) * | 1932-02-04 | 1933-05-30 | Emery Industries Inc | Method of cleaning fabrics |
| US2388962A (en) * | 1938-01-24 | 1945-11-13 | Allied Chem & Dye Corp | Dry cleaning composition |
| US2476554A (en) * | 1941-03-20 | 1949-07-19 | Continental Oil Co | Method of inhibiting deterioration of organic compounds |
| US2517895A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
| US3117152A (en) * | 1960-05-10 | 1964-01-07 | Stamford Chemical Ind Inc | Substantially neutral magnesium salt of a phosphoric acid ester of oxethylated nonylphenol |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3546305A (en) * | 1967-12-01 | 1970-12-08 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
| US20080274935A1 (en) * | 2007-05-01 | 2008-11-06 | Enviro Tech International, Inc. | Detergent Composition for Halogenated Dry Cleaning Solvents |
| US7803747B2 (en) | 2007-05-01 | 2010-09-28 | Enviro Tech International, Inc. | Detergent composition for halogenated dry cleaning solvents |
Also Published As
| Publication number | Publication date |
|---|---|
| BE700247A (enrdf_load_stackoverflow) | 1967-12-21 |
| NL6709211A (enrdf_load_stackoverflow) | 1969-01-07 |
| GB1150837A (en) | 1969-05-07 |
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