CA1070758A - Phenolic resin and battery separator impregnated therewith - Google Patents

Phenolic resin and battery separator impregnated therewith

Info

Publication number
CA1070758A
CA1070758A CA279,564A CA279564A CA1070758A CA 1070758 A CA1070758 A CA 1070758A CA 279564 A CA279564 A CA 279564A CA 1070758 A CA1070758 A CA 1070758A
Authority
CA
Canada
Prior art keywords
resin
resole resin
composition
battery separator
percent
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
CA279,564A
Other languages
French (fr)
Inventor
John R. Leblanc
Harold P. Higginbottom
William D. Burke
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.)
Monsanto Co
Original Assignee
Monsanto 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 Monsanto Co filed Critical Monsanto Co
Application granted granted Critical
Publication of CA1070758A publication Critical patent/CA1070758A/en
Expired legal-status Critical Current

Links

Classifications

    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M50/00Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
    • H01M50/40Separators; Membranes; Diaphragms; Spacing elements inside cells
    • H01M50/409Separators, membranes or diaphragms characterised by the material
    • H01M50/44Fibrous material
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/10Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/09Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/09Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098Metal salts of carboxylic acids
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M50/00Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
    • H01M50/40Separators; Membranes; Diaphragms; Spacing elements inside cells
    • H01M50/409Separators, membranes or diaphragms characterised by the material
    • H01M50/411Organic material
    • H01M50/429Natural polymers
    • H01M50/4295Natural cotton, cellulose or wood
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00Electrolytes
    • H01M2300/0002Aqueous electrolytes
    • H01M2300/0005Acid electrolytes
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10Energy storage using batteries

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cell Separators (AREA)
  • Secondary Cells (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE
The invention relates to an improved phenol-aldehyde resole resin composition for battery separa-tors and a fibrous battery separator impregnated with the composition. Said composition comprising a re-sole resin with particular soluble hydroxy organic salts that do not salt out and improve the oxidation resistance of the battery separators.

Description

5~3 ~

PHENOLIC RESIN AND BATTERY SEPARATOR IMPR-EGNATED THEREWITH
BACKGROUND OF THE INVENTION
This invention relates to an improved composition of a phenol-aldehyde resin containing a particular type of salt and to the cellulosic fibrous battery separator impregnated with the composition.
Permeable cellulosic fibrous battery separators are used extensively in batteries of ei-ther the conventional wet lead-acid type or the so-called "dry charge" lead~acid type. It is necessary that -the fibrous structures -thereof be protected from attack by the acid employed in the batteries. Therefore, when cellulosic fibrous battery separators are employed, they con-sist of cellulosic sheets impregna-ted with a phenol-aldehyde type of resin, which, when advanced to the infusible state, pro-tects the fibers of the cellulosic sheet from attack by the acid.
The phenolic resin employed in battery separators are usually water base resole liquid resins or solvent-containing "varnishes". In order to produce satisfactory battery separator properties the resins are generally supplied in a pH range of about 7.0-8.0, which is accomplished by neutralizing most of the basic catalyst employed in forming the resin. According to -the acid employed for neutralization, either an insoluble salt or a soluble salt may be present.
The insoluble salt is removed by fil-tration, while the soluble salt is left in the resin. In the latter case~ the choice of relatively inexpensive acids is quite limited. Thus, hydrochloric acid cannot be used because chloride has a delete-rious effect on batteries. Acetic acid is volatile and may come 1~ ,, ~ID'7~758 off during cure of the separator, causing the pH to rise and thus producing a dark, brittle separator.
Sulfuric acid is used and the commonly formed salt is sodium sulfate, since the resole is often catalyzed wi-th sodium hydroxide. While this salt is generally water soluble in the resole, it will precipitate out as the decahydrate if the resin solids are too high, or if the temperature of the resin becomes too low. Resin solids level can be adjusted to prevent precipi-tation due to that factor, but precipitation due to low tempera-ture is a cold weather problem and generally happens in storagetanks of the battery separator producer. Since there are usu-ally no facilities for heating such -tank, the resin may become unsatisfactory for use due to the precipitate.
Thus, it would be beneficial to neutralize with an acid having none of the above problems. A class of hydroxy organic acids were found to be beneficial. The hydroxy acids are se lected from the group consisting of citric, tartaric and lactic or mixtures thereof. Not only does it eliminate the salting out problem, but, surprisingly the separators made from the resin containing polyacid salts had improved oxidation resist-ance, an important property, over a similar base resin con-taining sodium sulfate salt.
SUMMARY OF THE_INVENTION
The present invention relates to an improved resole resin composition for battery separators comprising:
A. a resole resin formed as the reaction product of about lo O to 3.0 mols of formaldehyde per mol of phenol in the presence of an alkaline catalyst, the 1~7~7~8 improvement comprising having present:
B. an alkaline hydroxy organic acid salt formed by neutralizing said resole resin with sufficient hydroxy organic acid to provide said resole resi.n with a pH of 7 to 9O
The present invention also relates to an improved cellu-losic fibrous permeable battery separator impregnated with a resole resin composition comprising:
~. a resole resin formed as a reaction product of about 1.0 to 3.0 mols of formaldehyde per mol of phenol in the presence of an alkaline catalyst, the improvement comprising having present:
B. an alkaline hydroxy organic acid salt formed by neutralizing said resole resin with sufficient hydroxy organic acid to provide said resin wi~h a pH
of 7 to 9.
Any phenol-aldehyde resin may be employed in the prac-tice of this invention. Par-ticularly usefull however, are the phenol-formaldehyde resins which are generally prepared by the reaction of about 1.0 -3.0 mols of formaldehyde per mol of phenol in the presence of appropriate catalysts~ The phenol-; 2~ formaldehyde resins may be either a one-stage resin recovered in water, a one~stage resin recovered in a water-organic solvent.
The preparation of these resins is generally well-known and the type of phenol-formaldehyde resin obtained depends upon the ratio of formaldehyde to phenol and the catalyst chosen for the '' L~ _ ~07 [)75~3 reaction. As is well known in the art, the catalyst employed in the reaction is basic in nature. The preferred phenol-alde-hyde resin to be employed in the practice of this invention is a phenol-formaldehyde resin prepared by reacting 1.0-3.0 mols of formaldehyde per mol of phenol in the presence of an alkaline catalyst and wherein the reaction product is recovered in water.
The phenol-formaldehyde resin employed in the practice of this invention should also have a water tolerance of 0.1 volume of wa-ter per equal volume of resin to greater than 50 volumes of water per volume of resin. However, as a practical limit, the water tolerance should be 1 to 4 volumes of water per one volume ~i of resin or a water dilutability of 100 to 400 percen-t.
After the formation of -the resole resin under alkaline conditions at from 60 to 100C. using 0.03 to 1.00 mols of alka-line catalysts, e.g. sodium hydroxide or potassium hydroxide per100 parts of phenol to a free formaldehyde end point of 1 to 4 percent, the resole is generally diluted to a solids content of 40 to 60 percent by weight with a solvent such as water or alcohol or mixtures thereof and neutralized with a hydroxy or-ganic acid to a pH of from about 7 to 9. The hydroxy organicacids found to give the resin unexpectedly high salt stability with` no salt precipitation at low storage temperatures were the acids of the group consisting of citric, tartaric and lactic or mixtures thereof. The acids produced sodium or potassium salts that do not salt-out or preclpitate out in the resole when stored at low temperatures, e.g. at about 3.0C.
This invention i5 also directed to a cellulosic fibrous permeable battery separator consisting of a permeable cellulosic fibrous sheet impregnated with -the resin composition of this in-75~

vention and wherein the phenol-aldehyde resin is advanced to the infusible state. The cellulosic fibrous sheet is treated with the composition of this invention by either the we-t-web sa-tura-tion method or the dry-web method. In either method, it may be desirable to dilute the resin composition in order to obtain the desired pickup. The treated cellulosic sheet is dried to remove excess solvent and is then subjected to a temperature of about 150C. to about 300C. in order to advance the phenol-aldehyde resin to an infusible state. The time of exposure of the treated cellulosic fibrous sheet to these temperatures will vary from approximately 30 minu-tes at 150C. to at least one minute at 300C. In addition, the cellulosic fibrous ba-ttery separator is generally ribbed -to increase its resistance to degradation during use-thereof in a lead-acid battery. Cenerally, it is also desirable to impregnate the cellulosic fibrous sheet wi-th about 20-50 weight percent of the resin composition of this in-ven-tion.

An unneutralized resole resin was prepared by reacting 100 parts phenol with 120 parts 50 percent formalin at 77C.
with 0.06 mols NaOH to a free formaldehyde end point of 1.8 per-cent. The resin was diluted to about 47 percent solids with a mixture of 50 percent water and 50 percent methanol.
The resin was divided into two portions, one being neutralized to a pH of 7O7 with sulfuric acld (I) and one to 7.85 ~IV) with citric acid. Portions of these two resins were then blended l:l (II) and l part sulfuric acid neutralized: 3 parts citric acid neutralized (III).
The four resins were refrigera-ted at 3C. and observed .

~7~75~
C-06-12~0~25 for salt precipitation. After about 24 hours, a heavy precipi-tate was no-ted in I, with progressively lesser amounts in II and III and there was no precipitate in IV.

The resins were checked for oxidaticn resistance, a key property~in battery separators. Cotton linters paper of 20 mils thickness was passed through a bath of each resin diluted to about 25 percent solids. The paper was then passed through squeeze rolls and dried 30 minutes at 180C. to cure the resin.
This gave a cured resin content of approximately 25 percent.
The papers were then tested for oxidation resistance by boiling 3 hours in a solution of sulfuric acid and potassium di-chromate, after which they were washed, dried and weighed to ob-tain the loss in weight from the original value. This weight lS loss is expressed as the oxidation resistance. The values ob-tained were:

Resin Percent weight_loss I 57.3 II 42.7 III 39.2 IV 37.2 Thus, the surprising superiority of citric acid over sulfuric acid is demonstrated, not only in the salt precipita-tion problem, but also in oxidation resistance.
It was also found that the presence of the citrate salt has no deleterious effect on the wetting or rewetting character-istics of the separators.
The use of citric acid for neutralization applies to any ~t7~758 typical battery separator resin, i.e., resole resins generally having a formaldehyde~phenol mol ratio of about 1~0-3.0/1 usually catalyzed by alkali metal bases, such as sodium or potassium, in the range of 0.03-1.03 mols per mol of pheno:L charged. Depend-ing upon the actual level of basic ca-talyst used, the citric acid quantity should be such as to bring the final resin pH into the range of about 7-8 preferably.
The example given here is not meant to limit -the acid used to citric. Other hydroxy organic acids such as lactic, tartaric, etc. gave similar results.

Claims (13)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. An improved resole resin composition for battery separators comprising:
A. a resole resin formed as the reaction product of about 1.0 to 3.0 mols of formaldehyde per mol of phenol in the presence of an alkaline catalyst, the improvement comprising having present:
B. an alkaline hydroxy organic acid salt formed by neutralizing said resole resin with sufficient hydroxy organic acid to provide said resole resin with a pH of 7 to 9.
2. A composition of Claim 1, wherein said hydroxy organic acid is citric, tartaric, lactic or mixtures thereof.
3. A composition of Claim 1, wherein said alkaline catalyst is sodium hydroxide, potassium hydroxide or mixtures thereof.
4. A composition of Claim 1, wherein said salt is sodium citrate, sodium tartrate, sodium lactate, potassium citrate, potassium tartrate, potassium lactate or mixtures thereof.
5. A composition of Claim 1, wherein said resole resin has been advanced to a free formaldehyde end point of from about 1 to 4 percent and is water soluble, having a water dilutability of from 100 to 400 percent.
6. A composition of Claim 1, wherein said resole resin is a solution having from about 40 to 60 percent resin solids by weight and contained in a solvent selected from the group con-sisting of water and alcohol or mixtures thereof.
7. An improved cellulosic fibrous permeable battery separator impregnated with a resole resin composition compris-ing:
A. a resole resin formed as a reaction product of about 1.0 to 3.0 mols of formaldehyde per mol of phenol in the presence of an alkaline catalyst, the improvement comprising having present:
B. an alkaline hydroxy organic acid salt formed by neutralizing said resole resin with sufficient hydroxy organic acid to provide said resin with a pH
of 7 to 9.
8. A battery separator of Claim 7 wherein said hydroxy organic acid is citric, tartaric, lactic or mixtures thereof.
9. A battery separator of Claim 7, wherein said alka-line catalyst is sodium hydroxide, potassium hydroxide or mix-tures thereof.
10. A battery separator of Claim 7, wherein said salt is sodium citrate, sodium tartrate, sodiurn lactate, potassium citrate, potassium tartrate, potassium lactate or mixtures thereof.
11. A battery separator of Claim 7, wherein said resole resin has been advanced to a free formaldehyde end point of from about 1 to 4 percent and is water soluble, having a water di-lutability of from 100 to 400 percent.
12. A battery separator of Claim 7, wherein said resole resin is a solution having from about 40 to 60 percent resin solids by weight and contained in a solvent selected from the group consisting of water and alcohol or mixtures thereof.
13. A battery separator of Claim 7, wherein said resin composition comprises about 20-50 percent by weight of the separator.
CA279,564A 1976-06-01 1977-05-31 Phenolic resin and battery separator impregnated therewith Expired CA1070758A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US69127676A 1976-06-01 1976-06-01

Publications (1)

Publication Number Publication Date
CA1070758A true CA1070758A (en) 1980-01-29

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ID=24775878

Family Applications (1)

Application Number Title Priority Date Filing Date
CA279,564A Expired CA1070758A (en) 1976-06-01 1977-05-31 Phenolic resin and battery separator impregnated therewith

Country Status (5)

Country Link
US (1) US4075403A (en)
AU (1) AU508453B2 (en)
CA (1) CA1070758A (en)
FR (1) FR2353962A1 (en)
GB (1) GB1553764A (en)

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR799269A (en) * 1935-01-31 1936-06-10 Hermann Frenkel Process for the production of resistant coatings on wood
US2591754A (en) * 1945-05-21 1952-04-08 Auto Lite Battery Corp Battery separator
US2543137A (en) * 1946-04-12 1951-02-27 Texon Inc Battery separator
US2662106A (en) * 1951-08-04 1953-12-08 Us Rubber Co Battery separator
US2678961A (en) * 1952-12-23 1954-05-18 Us Rubber Co Battery separator and method of making same
US2850559A (en) * 1955-01-10 1958-09-02 Texon Inc Battery separator and method of making same
US3247025A (en) * 1963-08-29 1966-04-19 Monsanto Co Phenolic resin and battery separator impregnated therewith
DE1279795B (en) * 1965-01-29 1968-10-10 Grace W R & Co Process for the production of a microporous battery separator
US3382213A (en) * 1966-05-12 1968-05-07 Gen Electric One-stage resin and process for preparing same comprising reacting a spaced polyphenol and an aldehyde
US3703494A (en) * 1971-03-01 1972-11-21 Monsanto Co Resole varnishes wherein phenol is alkylated with a dicyclopentadiene-containing mixture and then condensed with formaldehyde to produce the resole
US3893871A (en) * 1974-01-09 1975-07-08 Monsanto Co Phenolic resin and battery separator impregnated therewith
US3926679A (en) * 1974-01-09 1975-12-16 Monsanto Co Phenolic resin and battery separator impregnated therewith

Also Published As

Publication number Publication date
AU508453B2 (en) 1980-03-20
FR2353962B1 (en) 1981-12-11
FR2353962A1 (en) 1977-12-30
US4075403A (en) 1978-02-21
AU2567077A (en) 1978-12-07
GB1553764A (en) 1979-10-10

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