US3796666A - Composition and method for dispersing proteinaceous stains - Google Patents
Composition and method for dispersing proteinaceous stains Download PDFInfo
- Publication number
- US3796666A US3796666A US00260650A US3796666DA US3796666A US 3796666 A US3796666 A US 3796666A US 00260650 A US00260650 A US 00260650A US 3796666D A US3796666D A US 3796666DA US 3796666 A US3796666 A US 3796666A
- Authority
- US
- United States
- Prior art keywords
- composition
- aminothiol
- dispersing
- sodium
- compositions
- 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
- 239000000203 mixture Substances 0.000 title abstract description 39
- 238000000034 method Methods 0.000 title description 7
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 abstract description 15
- 239000003599 detergent Substances 0.000 abstract description 13
- 239000004094 surface-active agent Substances 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 230000003139 buffering effect Effects 0.000 abstract description 5
- 102000004169 proteins and genes Human genes 0.000 abstract description 5
- 108090000623 proteins and genes Proteins 0.000 abstract description 5
- 230000008961 swelling Effects 0.000 abstract description 3
- 125000000129 anionic group Chemical group 0.000 description 12
- 239000004744 fabric Substances 0.000 description 8
- -1 sodium alkylsulfates Chemical class 0.000 description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000007844 bleaching agent Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000008234 soft water Substances 0.000 description 5
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004453 electron probe microanalysis Methods 0.000 description 4
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 4
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- GNETVHIDZPYGGD-UHFFFAOYSA-N 1-aminoethanethiol;hydrochloride Chemical compound Cl.CC(N)S GNETVHIDZPYGGD-UHFFFAOYSA-N 0.000 description 1
- NOLWAGXBBKJFEE-UHFFFAOYSA-N 1-aminosulfanylethanol Chemical compound CC(O)SN NOLWAGXBBKJFEE-UHFFFAOYSA-N 0.000 description 1
- UYNKVBYVIGUBMK-UHFFFAOYSA-N CC.OOP(=O)OP(O)=O Chemical class CC.OOP(=O)OP(O)=O UYNKVBYVIGUBMK-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102000005158 Subtilisins Human genes 0.000 description 1
- 108010056079 Subtilisins Proteins 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000009895 reductive bleaching Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3427—Organic compounds containing sulfur containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
Definitions
- a detergent composition is formulated to contain an aminothiol of the formula HS(CH NH where n is from 2 to 4, a protein swelling anionic surface-active agent and a pH buffering compound. This detergent composition has particular utility for dispersing proteinaceous stains.
- the present invention provides a dispersing composition for proteinaceous stains comprising an aminothiol of the general formula:
- n is from 2 to 4
- a protein-swelling anionic surface-active agent in which n is from 2 to 4
- one or more pH buffering compounds such that an aqueous solution of the composition containing 0.1 weight percent of aminothiol has pH in the range of 7 to 12.
- the protein-swelling action of the surface-active agent renders the protein stains more susceptible to attack at their disulfide linkages by the sulfhydryl compounds.
- the latter are effective in mild conditions and at low concentrations to break the bonds holding together the proteinaceous stains so that they are more readily dispersible by Washing.
- aminoethanethiol (sometimes known as aminothioethanol or cysteamine), which is the compound of the general formula given above in which n is 2.
- the compounds of the general formula given above are compatible with anionic surface-active agents and are effective in midly alkaline conditions, for instance, from pH 7 to 12, preferably from 8 to 11.
- Suitable anionic detergents are those which have strong protein-swelling tendencies, particularly those with hydrophobic chains of about 12 carbon atoms, such as sodium alkylsulfates having about 8 to 14 carbon atoms, and
- Suitable pH buffering compounds are known in the art. It is an advantage of these compositions that many of the compounds suitable as pH buffers are those employed in conventional alkaline detergent compositions, and, whether acting as buffers or not, these compounds may be incorporated in the compositions. Thus, there may be present water-soluble phosphates and polyphosphates, carbonates, silicates, borates, and, if desired, neutral salts such as chlorides, or sulfates. Alkaline organic sequestrant and detergency building salts such as the aminopolycar- 'boxylates such as nitrilotriacetates, or ethane hydroxy diphosphonates and the like may also be used.
- the ratio of anionic surface-active agent to aminothiol is not very critical, but is preferably at least 1:2 molar so that enough anionic is present.
- the upper limit of this ratio is determined by practical and economic considerations and may be as high as 10:1 or more.
- a generally useful range is 1:2 to 8: 1, but normally a molar ratio of about 2:1 to 1:1 is suitable and convenient.
- the proportion of pH buffering agent muct be sufficient to controlthe pH as specified above.
- deterency builders When deterency builders are used they can be present in the proportions usual in built detergent compositions, and often as such provide ample pH buffering capacity.
- the actual level of aminothiol in the compositions can vary widely according to the nature of the composition and the concentration at which it is intended to be used, and the preferred in-use concentrations will be described below.
- reducing bleaching agents may be included in these compositions, but oxidizing agents are incompatible.
- Suitable reducing bleaches are, for example, sodium borohydride, sodium dithionite and hydrazine hydrate.
- nonionic, semipolar or zwitterionic surface-active agents may be included.
- Suitable nonionic agents include the well-known condensation products of ethylene oxide on fatty alcohols, alkylphenols, fatty acids, fatty amines and sorbitan esters.
- Semipolar agents are, for example, long-chain tertiary amine oxides or phosphine oxides, such as dodecyldimethylamine oxide.
- Suitable zwitterionic agents include the quaternary ammonium betaines, sulfobetaines, and sulfatoor sulfito-betaines, for example, octadecyldimethyl ammonio-propane sulfonate or -hydroxypropane sulfonate, and dodecylbenzyl dimethyl ammoniopropane sulfonate.
- compositions may also contain, when appropriate and compatible, the usual minor ingredients of such compositions.
- These include suds-controlling agents, soil-suspending agents such as carboxymethylcellulose, polymers of maleic anhydride and methylvinylether and the like, enzymes, optical brighteners, tarnish-inhibitors, bacteriostats or bactericides, colors and perfumes.
- the invention also embraces a method of dispersing a proteinaceous stain on the substrate stained therewith which comprises treating the stain with an aqueous solution of a composition of the invention while maintaining the pH of said solution in the range 7 to 12 preferably 8 to 11.
- composition containing fl-aminoethanethiol it is preferred to use a composition containing fl-aminoethanethiol.
- stained substrates may be treated by soaking or washing them, preferably with agitation, in solutions of the specified strength at temperatures in the usual washing range, for instance, from 10 to 100 C., especially from 20 to 70 C. An overnight soak at about 20 C. (or ambient) temperature is effective. At higher temperatures, stain dispersal can be obtained more quickly. Unlike enzymes, these compounds are not destroyed or rendered ineffective by high temperature up to about 100 C. Thus, they are suitable for use in compositions intended for automatic dishwashing machines where very hot water is commonly employed.
- EXAMPLE I A standard blood stained test cloth (cotton), so-called EMPA 111 obtained from EMPA, Unterstrasse 11, 9001 St. Gall, Switzerland was given a preliminary wash in soft water at 40 C. and dried.
- a solution was prepared containing 1 g. aminoethanethiol and 4 g. sodium lauryl sulfate (approx. equimolar proportions) per liter in soft water with pH buffered to 9.5.
- a two-inch square piece of the above test cloth was allowed to soak overnight (16 hours) in 1 liter of the above solution, initially at 21 C. but allowed to cool naturally to about C. (ambient temperature). The cloth was then rinsed in soft water and allowed to dry.
- a comparative test was made in which the test cloth was treated similarly except in that it was soaked in a solution of 5 g. per liter of a commercial enzymeand perborate-containing heavy-duty anionic detergent composition.
- the stain removal by the aminoethanethiol/sodium lauryl sulfate mixture was as good as or better than by the conventional enzymeand peroxy bleach-containing detergent composition.
- EXAMPLE II Test method for protein stain dispersion Standard blood-stained cotton fabric (EMPA 111, supplied by EMPA, St. Gall, Switzerland) was pretreated by washing at 40 C. in soft water for minutes. It was rinsed and air dried, and its reflectance measured with an BEL (Evans Electroselenium Ltd.) spectrophotometer using a No. 601 filter.
- Test pieces of the pretreated fabric were soaked and/or washed in test solutions of compositions according to the invention and of reference compositions.
- Test solutions for soaking were prepared, and the test pieces were added, at C., being then allowed to cool naturally during the period of the soak.
- the test pieces were then The product of composition B of Example II was compared with the same, but omitting aminothiol and sodium lauryl sulfate and replacing with moisture (normal) to make up the formula weight, coded J.
- the. test pieces were given a 10 min. wash, without any soak treatment, at various temperatures, followed by the usual rinse and drying.
- Test pieces as in Example II were given an overnight soak and a 10 min. wash at 60 C.
- the cleaning was found to improve in the order composition A to composition D.
- a dispersing composition for proteinaceous stains consisting essentially of (a) an aminothiol of the general formula HS (CH NH wherein n is from 2 to 4; (b) a protein swelling anionic surface-active agent; and
- a pH bufiering compound selected from the group consisting of water-soluble phosphates, polyphosphates, carbonates, silicates, and borates in an amount suflicient to impart a pH in the range of 7 to 12 to an aqueous solution of the composition containing 0.1 weight percent of aminothiol,
- the molar ratio of the anionic surface-active agent to the aminothiol is at least 1:2.
- composition of claim 1 wherein the molar ratio of anionic surface-active agent to aminothiol is from 1:2 to 8: 1.
- composition of claim 2 wherein the anionic surface-active agent is an alkyl sulfate having 8 to 14 carbon atoms.
- composition of claim 2 wherein the anionic surface-active agent is a soap having 8 to 14 carbon atoms.
- composition of claim 3 wherein the aminothiol is fi-aminoethanethiol.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2801671 | 1971-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3796666A true US3796666A (en) | 1974-03-12 |
Family
ID=10268920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00260650A Expired - Lifetime US3796666A (en) | 1971-06-15 | 1972-06-07 | Composition and method for dispersing proteinaceous stains |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3796666A (enExample) |
| BE (1) | BE784890A (enExample) |
| CA (1) | CA970238A (enExample) |
| DE (1) | DE2228930A1 (enExample) |
| FR (1) | FR2141895A1 (enExample) |
| IT (1) | IT956566B (enExample) |
| NL (1) | NL7208168A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11680958B2 (en) | 2018-09-28 | 2023-06-20 | Taiwan Semiconductor Manufacturing Company, Ltd. | Particle image velocimetry of extreme ultraviolet lithography systems |
| US11824101B2 (en) | 2018-09-28 | 2023-11-21 | Taiwan Semiconductor Manufacturing Co., Ltd. | High aspect ratio gate structure formation |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050015A3 (en) * | 1980-10-14 | 1982-06-09 | Yuken Industries Co. Ltd. | Cleaning composition |
-
1972
- 1972-06-07 US US00260650A patent/US3796666A/en not_active Expired - Lifetime
- 1972-06-14 CA CA144,682A patent/CA970238A/en not_active Expired
- 1972-06-14 FR FR7221353A patent/FR2141895A1/fr not_active Withdrawn
- 1972-06-14 BE BE784890A patent/BE784890A/xx unknown
- 1972-06-14 DE DE19722228930 patent/DE2228930A1/de active Pending
- 1972-06-15 NL NL7208168A patent/NL7208168A/xx unknown
- 1972-06-15 IT IT25677/72A patent/IT956566B/it active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11680958B2 (en) | 2018-09-28 | 2023-06-20 | Taiwan Semiconductor Manufacturing Company, Ltd. | Particle image velocimetry of extreme ultraviolet lithography systems |
| US11824101B2 (en) | 2018-09-28 | 2023-11-21 | Taiwan Semiconductor Manufacturing Co., Ltd. | High aspect ratio gate structure formation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2141895A1 (enExample) | 1973-01-26 |
| DE2228930A1 (de) | 1972-12-21 |
| IT956566B (it) | 1973-10-10 |
| NL7208168A (enExample) | 1972-12-19 |
| BE784890A (fr) | 1972-12-14 |
| CA970238A (en) | 1975-07-01 |
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