CA1038253A - Composition and process for drying water-wet surfaces - Google Patents

Composition and process for drying water-wet surfaces

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Publication number
CA1038253A
CA1038253A CA216,180A CA216180A CA1038253A CA 1038253 A CA1038253 A CA 1038253A CA 216180 A CA216180 A CA 216180A CA 1038253 A CA1038253 A CA 1038253A
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CA
Canada
Prior art keywords
composition
weight
trichloro
trifluoroethane
ethylenediamine
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
Application number
CA216,180A
Other languages
French (fr)
Other versions
CA216180S (en
Inventor
Spyridon Stavras
Hans R. Giger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Application granted granted Critical
Publication of CA1038253A publication Critical patent/CA1038253A/en
Expired legal-status Critical Current

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Classifications

    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26DRYING
    • F26BDRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B5/00Drying solid materials or objects by processes not involving the application of heat
    • F26B5/005Drying solid materials or objects by processes not involving the application of heat by dipping them into or mixing them with a chemical liquid, e.g. organic; chemical, e.g. organic, dewatering aids

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Detergent Compositions (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

TITLE OF THE INVENTION

COMPOSITION AND PROCESS FOR DRYING WATER-WET
SURFACES
ABSTRACT OF THE DISCLOSURE
A liquid composition, and a process using the com-position, for drying water-wet surfaces, which composition comprises:
(1) 1,1,2-trichloro-1,2,2-trifluoroethane, (2) 0.01 to 10 weight %, based on the weight of 1,1,2-trichloro-1,2,2-trifluoroethane, of a solute phosphate salt of (i) a monoalkyl or dialkyl phosphate ester, or a mixture thereof, wherein each alkyl group contains 6 to 20 carbon atoms, and (ii) sufficient saturated aliphatic amine con-taining 6 to 20 carbon atoms and having 1 to 3 alkyl groups attached to the amine nitrogen atom to at least neutralize the phosphate ester, and (3) 0.025 to 1 weight %, based on the weight of 1,1,2-trichloro-1,2,2-trifluoroethane, of a partially oleated N,N,N',N'-tetrakis-(2-hydroxy-propyl)ethylenediamine containing an average of about two oleate ester groups and quaternized with 0.7 to 1.7 moles (per mole of the ethylenediamine) of dimethyl sulfate.

Description

3ACKGROUND~OF THE INVENTION
1. Field o~ the Inve _ ion This invention relates to composition and process for drying water-wet ~urfaces.
2. DescriPtion of the Prior Art It is known that a water-wet æurface can be dried by
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expo~in~ 8uch ~ surface to a dense water immiscible organlc liquid, optionally containing a surfactant. The water immis-cible organic liquid can be agitated by boiling or by mechanical means. U.S. Patent ~,397,150 disclose~ a dlsplacement drying process to remove water from a surface,and to prevent rust from forming on a ferrous ~ur~ace, by expo ing the surface to a compo~ition comprising 1,1,2-trichloro-1,2,2-tri~luoroethane and 0.01 to 10 weight %, ba~ed on the weight of 1,1,2-trichloro-1,2,2-trifluoroethane, of a solute phosphate salt of a monoalkyl or dialkyl phosphate ester, or a mixture thereof, wherein each alkyl group contains 6-20 carbon atoms, and a saturated ali-phatic amine containing 6 to 20 carbon atoms and having 1 to ~ -alkyl groups attached to the amine nitrogen, said amine being employed in an amount at least sufficient to substantially completely neutralize the phosphate ester but not exceeding a 10% exces3 over the stoichiometric amount necessary to sub-stantially completely neutralize the ester. Such a composition is excellent for drying water-wet, machined metal parts, ~uch as bearings ancl valve components, plastic parts and electro-plated gold or silver surfaces, such as those used in making ~ewelry. However, when used for refined drying, such as that necessary to dry water-wet,glass crystal surfaces or silicon surfaces used in electronic circuitry, difficulties may be encountered in that very small droplet~ of water or small deposits of residue may be retained and/or formed on the sur-face. In the ca~e o~ gla~ crystals this seriously detract~
from the aesthetic appearance o~ the cry~tal and in the case of silicon surfaces thi~ interfere~ with the functionality of the surface as an electronic component.
~o U.S. Patent ~,2~,011 discloses the use, as a dry-cleaning fluid, of 1,1,2-trichloro-1,2,2-trifluoroethane containing 0.05 to 0.5 weight % of a partially oleated N,N,N',N'-tetrakis-(2-hydroxypropyl)ethylen~diamlne quaternlzed ~ith 0.7 to 1.7 molar proportions of dimethyl sulfate. Patentees dis-close that ~uch a dry-cleaning fluld will di~solve a s~all concentration of water.
SUMMARY OF T~E I~VENTIO~
It is an ob~ect of this invention to provide a liquid composition and a proces~ for itA use in refined d~ying operations involving a water-wet surface, which composition and process avoid retention and/or formation of water droplets and residue spots on the dried æurface.
The present invention encompasses a liquld composition .
and a proces~ for drying water-wet ~urface~ therewith, the com-posi~ion compri~ing (1) 1,1,2-trichloro-1,2,2-trifluoroethane, t2) 0.01 to 10 weight %, based on the welght of 1,1,2-trichloro-1,2,2-tri~luoroethane, o~ a solute phosphate salt o~
(i) a monoalkyl or dialkyl phosphate ester, or a mixture thereof, wherein each alkyl group contains 6 to 20 carbon atoms, and -" (ii) sufficient saturated aliphatic amlne con-taining 6 to 20 carbon atom~ and having - 1 to 3 alkyl group~ attached to the amine nitrogen atom to at least neutralize the - phosphate eRter, and ~) 0.025 to 1 weight ~, ba~ed on the weight of 1,1,2-trlchloro-1,2,2-tri~luoroethane, of a ~- partially oleated N,N,NI,N~-tetrakis-(2-hydroxy-~0 propyl)ethylenediamine containing an averaee of about t~o oleate ester groups and quaternized with 0.7 to 1.7 mole~ (per mole of the ethylenediamine) of dimethyl sul~ate.
_ ~ _ .

~.038ZS3 DETAILED DESCRIPTION OF THE INVENTION
The following materials are useful in preparing the liquid composition of thi~ invention disclosed in the above summary.
me 1,1,2-trichloro-1,2,2-trifluoroethane i8 a well known and commercially available material.
e monoalkyl and dialkyl phosphate esters which are useful herein are those having the structure3 O O
,- ..
10~OP(OH)2 and (RO)2POH, respectively, wherein R is an aIkyl group containing 6 to 20 carbon atoms.
The exact nature of the alkyl group iB not critical except to the extent that it must contain the specified number of carbon atoms. It can be a straight chain group, such as hexyl, octyl, decyl, dodecyl, tridecyl, tetradecyl, hexadecyl or octadecyl, or a branched chain group, such as isooctyl, 2-ethylhexyl, i60- :
decyl, tert.-dodecyl, or such as is present in the branched chain alcohols known a~ oxo alcohols.
-~ me saturated aliphatic amines which are use~ul herein are those containing a total o~ 6 to 20 carbon atoms and having the structure R'N(R")2 wherein R' is an alkyl group and each R'l - is hydrogen or an alkyl group. mus, the amine can be a primary amine, such as he~ylamine, octylamine, 2-ethylhexylamine, 1,1,3,3-tetramethylbutylamine, decylamine, dodecylamine, tetra-decylamine, hexadecylamine or octadecylamine; a secondary amine, such as ethylbutylamine~ dipropylamine, hexylmethylamine, di-butylamine, decylmethylamlne, butyloctylamine, dodecylmethylamine, tetradecylmethylamine,dioctylamine or octadecylmethyla~ine, or a tertiary amine,such as triethylamine, decyldimethylamine, tri-~o butylamine, diethyloctylamine, tetradecyldimethylamine, hexa-decyldimethylamine, decyldibutylamine or octadecyldimethylamine.

.lxtures of amines, often ava~ a~le commerclally. can al~o be used.
The third es~ential component ln the compo~ition of this invention is a p~rtlally oleated NsN,N',N'-tetrakl~-(2-hydroxypropyl~ethylenediamine contalning an average of two oleate ester groups and quaternized wlth 0.7 to 1.7 moles of dimethyl ~ulfate per mole of diamine. These materials and their preparation are well known ln the art, such a~ represented -- by U.S. Patent 2 878 144 is8ued 17th March 1959 to Conbere et al, The preferred product is obtained by employing about 1.2 ; molar prop~rtion~ of dimethyl sulfate ln the quaternization reaction.
Th`e compositlon of this inventlon is prepared by first mixing the phosphate e~ter and the required amount of amine, usually in the presence of sufficient solvent or diluent to maintain the fluidity of the mixture during prepar~tion of the acid-base salt, me amount of amine present should be at least sufficient to sub~tantially completely neutralize the phoæphate ester, however, it should not exeeed an amount which is about 10% in exces9 of the 9tolchiometric amount .
nece8sary to substantially completely neutralize the phosphate ester. In general, about one mole of amine per mole of phos-phate ester 18 required to substantially completely neutralize the phosphate ester, In the neutralization of the diacidic monoalkyl ester, the second acldic hydrogen atom is not suf-flciently acidic to react with the amine. Substanti~lly com~
plete neutralization of the re~ctive acidic hydrogen ~tom3 in the phosphate ester is important slnce resldues of unneutr~llzed phosphate ester are difficult to remove from the surface. In 3 so~e cases, such acidic residues may lead to corrosion of the 8urface being dried. m e solvent or diluent is then removed and the de~ired amount of solute phosphate ~alt is di~solved in the :

103~253 1,1,2-trichloro-1,2,2-tri.fluoroethane solvent. Thereafter, the third component i6 added.
me solute phosphate salt of the alkyl phosphate e~ter and the saturated aliphatic amine is added to 1,1,2-trichloro-1,2~2-trifluoroethane in the amount of about 0.01 to 10 weight %, based on the weight of 1,1,2-trichloro 1,2,2-trifluoroethane present. Preferably, the amount of solute added is about 0.05 to 3~. The third component iB present in the composition of this invention in the amount of 0.025 to 1 weight .~ 10 %,based on the weight of 1,1,2-trichloro-1,2~2-trifluoroeth~ne, preterably 0.025 to 0.05%.
The preferred composition of this invention is that wherein the solute phosphate salt is prepared from ~a) a mixture of mono-(tridecyl) and bis-(tridecyl) phosphateæ neutralized : with 2-ethylhexylamlne; (b) a mixture Or monooctyl and dioctyl . phosphates,in which the octyl group is derived from oxooctyl alcohol (that is, prepared by the oxo process), neutral-.zed with 2-ethylhexylamine; and (c) a mixture of mono- and di-n-octyl and mono- and di-n-decyl phosphates neutralized with 2-ethylhexylamine, and the partially oleated diamine i~
dioleated N,N,N',N'-tetrakis-t2-hydroxypropyl)ethylenediamine.
: Suitable surfaces from which water can be removed in accordance with the composition and process of this invention are not limited to any particular material; they can comprise ~` any substantially water insoluble solid substance. The water to be removed from the surface can be in the form o~ a thin .. film, droplets of various sizes or adYorbed water held by ~- capi.lary attraction. The water can be substantially pure or - it can be a dilute solution of a salt, detergent or soap. Any . 3o such solute, however, should not be pre~ent in sufficient amount 1~3B2S3 `~ m~ke the water A ~olvent ror the 1,1,2-trichl~ro-1,2,2-trifluoroethane compo~ition~ Typic&l exAmples of surfaces that are p~rtlcularly dlfflcult to dry properly by pre~ently known methods, but which are currently and easily dried by treatment with the composition of this lnventlon, include the followlng:
a~ glas~ware, p~rticularly cry~talware, optlcal len!~es and glass plates which are uRed a8 sub~trate~ for electronic circuitry;
b) epoxy and phenolic resin 3urfaces, such as those used ln manu~acturlng electronic circuit boards, c~ sillcon surfaces, such as sillcon wafers and silicon chips whlch are used a8 seml-conductors;
d) matte nickel sur~ces, such a~ tho~e ~ormed by electrode-deposltion on brass or copper to obtain a decoratlve satln-like flnish;
- e~ alumlna surfaces, such as those prepared for u~e as electronic substr~tes, and f) anodized aluminum parts used for decor~tive effects.
In addition, the composition o~ this lnventlon can be used to dry other surfaces, such as those prepared of ferrous metal~, nickel and it~ alloy3, chromium and its alloys, ~tainless steels, copper, bras~, bronze, sllver and alu~inum. Plastic surfaces also can be treated ~or water removal wlth the compositlon of this invention. Included are surfaces wh~ch are fabrlcated from plastics such as nylon, polyethylene, poly-propylene, polyvinylchloride and ABS (acrylonltrile/butadiene/
styrene) resin~, As expected, surface~ of highly water reactive metalæ, such as the alkali metals, cannot be drled with this composition.

; -7-~38253 The process of this invention is carrled out by exposing the water-wet sur~ace with the co~position of this - -Lnvention. mis exposure can be accomplished by contacting the surface with the compositlon by spraying, brushing or any other means whereby the composition is applied to or passed over the surf'ace, for example, by immersing the 3urface in the composition. Water removal can be carried out at ambient tem-perature, although lower or higher temperatures, up to the boiling point of the drying composition, can be used. For the greatest efficiency in drying it is preferred that the com-position be used at its boiling point. In pressurized system~
temperatures above the normal atmospheric pressure boiling point of the composition can be used, although no special advantage is gained thereby. me time of treatment is not critical since a substantial amount of water removal is accom-plished upon immediate contact of' the sur~'ace with the drying composition. As a practical matter, the sur~ace will generally be in contact with the co~position f'or about one minute9 although longer or shorter times can be used.
The treated surface can be rinsed with a nonaqueous organic solvent to remove traces Or the solute. This step may - be omitted if such traces are not detrimental to the ultimate ~ use of the surface. If used, the organic solvent is allowed -- to evaporate from the surface, leaving the surface completely ;~ clean and dry. Any organic solvent can be used provided it i~
water free, dissolves the traces of solute from the surface and does nok attack the surface. A preferred solvent, because it dissolves the solutebutdoes not, in general, harm the surf~ace, is 1,1,2-trichloro-1,2,2-trifluoroethane, that is, the principal component of the composition of this invention.

~Q3~2~3 The trichlorotrifluoroethane need not be pure; mixtures thereof with anhydrous alcoholsl methylene chloride or acetone, all well known in the art~ can also be used.
An apparatus which is particularly useful in drying water-wet articles is disclosed in U.S. Patent No. 3,386,181 issued 4th June 1968 to W.R. Steinacker. This patent discloses an apparatus wherein is carried out the process of contacting the water-wet article with a drying composition by immersing the article in a turbulent zone of the drying composition, allow-ing the displaced water to float to the surface of the dryingcomposition in a quiescent zone, and thereafter removing the displaced water. Such an apparatus requires the water phase to separate rapidly.
The following example illustrates the composition and process of this invention; all parts and percentages are by weight.
- EXAMPLE
... .. _ Compositions were prepared, as shown in the following table, from 1,1,2-trichloro-1,2,2-trifluoroethane and the two solutes indicated (A and B). The compositions were placed in suitable containers and heated until they boiled. me following water-wet articles were placed in the boiling bath and thereafter were dipped into a bath of 1,1,2-trichloro-1,2,2-trifluoroethane (the residence time in each bath ranged from about 0.5 to 1.5 minutes): crystal glassware, an optical glass lens, an alumina electronic substrate, a phenolic electronic substrate and a matte surface of nickel. The results of a microscopic exa~ination of the treated surfaces are shown in the table.

. C

~ 03~2S3 Furthermore, the ab~ve described composi.tion~ were tested for phase separatlon in the following manner: a known qu~ntity of water was added to a ~ample of each composition and vigorously hand-shaken at room temperature (25C), then the Qample was allowed to re~t until 2 clear phases were observed lndicatlng complete separation of water from the compositlon.
The phase separation time~ are shown in the table, TABLE

DRYING AND PHASE SEPARATION EFFECTIVENESS OF
1,1,2-TRIC~LOR0~1,2,2-TRIFLUOROETHANE COMPOSITIONS

Phase Experiment Solute A Solute B Drying Separatlom No. Weight % Weighc ~ E~fectiveness Time (minutes~
1 0.28 0 Poor 3 2 0 0.05 Excellent 120 3 0 0,10 Excellent ~ 180
4 0 0.50 Excellent ~ 180 0.28 0,010 poor 3 6 0~28 0.025 Good 4 7 0.28 0.050 Excellent 4 ~ = greater than -~Solute A: mixture of about equimolar amounts of monoisooctyl :.and diisooctyl phosphates substantially completely neutralized with 2-ethylhexylamlne Solute B: N,N,N',N'-tetrakis-(2-hydroxypropyl~ethylenediamine dioleate quaternized with 1.23 moles (per mole of dioleate~ of dimethyl ~ulfate -;

Claims (11)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. Composition comprising:
(1) 1,1,2-trichloro-1,2,2,-trifluoroethane, (2) 0.01 to 10 weight %, based on the weight of 1,1,2-trichloro-1,2,2-trifluoroethane, of a solute phosphate salt of (i) a monoalkyl or dialkyl phosphate ester, or a mixture thereof, wherein each alkyl group contains 6 to 20 carbon atoms, and (ii) sufficient saturated aliphatic amine con-taining 6 to 20 carbon atoms and having 1 to 3 alkyl groups attached to the amine nitrogen atom to at least neutralize the phosphate ester, and (3) 0.025 to 1 weight %, based on the weight of 1,1,2-trichloro-1,2,2-trifluoroethane, of a partially oleated N,N,N',N'-tetrakis-(2-hydroxy-propyl)ethylenediamine containing an average of about two oleage ester groups and quaternized with 0.7 to 1.7 moles (per mole of the ethylenediamine) of dimethyl sulfate.
2. The composition of Claim 1 wherein each alkyl group of the phosphate ester contains eight carbon atoms and the saturated aliphatic amine is a monoalkylamine containing eight carbon atoms.
3. The composition of Claim 2 wherein said partially oleated N,N,N',N'-tetrakis-(2-hydroxypropyl) ethylenediamine is quaternized with about 1.2 moles of dimethyl sulfate.
4. The composition of Claim 3 wherein the amount of solute phosphate salt is 0.28%.
5. The composition of Claim 4 wherein the amount of the partially oleated N,N,N',N'-tetrakis-(2-hydroxypropyl) ethylenediamine is 0.025 to 0.05%.
6. Process for drying a water-wet surface by contacting the surface with the composition of Claim 1.
7. The process of Claim 6 using the composition of Claim 4.
8. The process of Claim 6 using the composition of claim 5.
9. The process of Claim 6 wherein the composition is at its boiling point during the contacting of the surface.
10. The process of Claim 6 wherein the surface, subsequent to contacting with the composition of Claim 1, is contacted with a nonaqueous organic solvent in which the phos-phate ester and the oleated ethylenediamine are soluble.
11. The process of Claim 10 wherein the nonaqueous organic solvent comprises 1,1,2-trichloro-1,2,2-trifluoroethane.
CA216,180A 1974-08-13 1974-12-17 Composition and process for drying water-wet surfaces Expired CA1038253A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US49707174A 1974-08-13 1974-08-13

Publications (1)

Publication Number Publication Date
CA1038253A true CA1038253A (en) 1978-09-12

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ID=23975345

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CA216,180A Expired CA1038253A (en) 1974-08-13 1974-12-17 Composition and process for drying water-wet surfaces

Country Status (8)

Country Link
JP (1) JPS5120792A (en)
BE (1) BE824539A (en)
CA (1) CA1038253A (en)
CH (1) CH611406A5 (en)
FR (1) FR2281778A1 (en)
GB (1) GB1492780A (en)
IT (1) IT1028163B (en)
NL (1) NL155585B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2522007A1 (en) * 1982-02-23 1983-08-26 Ugine Kuhlmann COMPOSITION FOR SURFACE WELDING
FR2527625A1 (en) * 1982-05-27 1983-12-02 Chloe Chemie COMPOSITION BASED ON FLUOROCHLOROHYDROCARBIDE, PHOSPHORIC ESTER AND CARBOXYLIC ACID

Also Published As

Publication number Publication date
JPS5120792A (en) 1976-02-19
DE2460209B2 (en) 1976-09-09
NL7500766A (en) 1976-02-17
IT1028163B (en) 1979-01-30
JPS544717B2 (en) 1979-03-09
NL155585B (en) 1978-01-16
CH611406A5 (en) 1979-05-31
DE2460209A1 (en) 1976-02-26
FR2281778A1 (en) 1976-03-12
GB1492780A (en) 1977-11-23
BE824539A (en) 1975-07-22
FR2281778B1 (en) 1977-07-01

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