US1833772A - Abating foaminess in glues - Google Patents
Abating foaminess in glues Download PDFInfo
- Publication number
- US1833772A US1833772A US430141A US43014130A US1833772A US 1833772 A US1833772 A US 1833772A US 430141 A US430141 A US 430141A US 43014130 A US43014130 A US 43014130A US 1833772 A US1833772 A US 1833772A
- Authority
- US
- United States
- Prior art keywords
- glue
- water
- glues
- base
- oil
- 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
- 239000003292 glue Substances 0.000 title description 55
- 239000002585 base Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000005018 casein Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 8
- 235000011941 Tilia x europaea Nutrition 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 239000003350 kerosene Substances 0.000 description 8
- 239000004571 lime Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 7
- 235000021240 caseins Nutrition 0.000 description 7
- 235000012054 meals Nutrition 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- 235000019610 cohesiveness Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 230000003405 preventing effect Effects 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 241000218645 Cedrus Species 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 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 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940051043 cresylate Drugs 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J189/00—Adhesives based on proteins; Adhesives based on derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
Definitions
- Glues prepared from mixtures of milk-casein with one or more of the vegetable seedmeals of commerce may likewise exh1b1t a a tendency to foam.
- Foam glues, from whatever source, are usually 1n mobility and cohesiveness, do not spread read1ly, and when applied to wood-veneers and the like give inferior joints.
- the resent invention relates to a method of abatmg or preventing the foaming tendency and improving the general character of such glues. It consists in adding to the wet glue (or preferably to the water in which the glue is to be dissolved) an oil WhlCh 1s practically insoluble in water, such as kerosene or other petroleum distillate less volatile than naphtha and lighter than an ordinary motor lubricant, or oil of cedar wood or other suitable oil, preferably together wlth a small amount of a phenolic substance such 'as' phenol, cresol or their sodium compounds, sodium phenate and sodium cresylate. These oils act as foam-abaters, while the phenolic 50 compound acts as a conditioning agent, im-
- t is experiment about 225 parts of cold water are measured into a glue-kettle provided with a mixing device. To this is added 3 parts of the antisfoam substance selected, and the mixer is started. Without interru ting the stirring, 100 parts of the glue powd r are added-and after stirring for twenty minutes the glue y is ready. The consistency of the glue at a this period is determined in'the Stormer viscosimeter, an instrument which consists of a cylinder rotatiu on a vertical axis between.
- baflies in a cup filled with the glue baflies in a cup filled with the glue.
- the number of rotations per minute is indicated on a dial.
- a viscous, sluggish glue will show few revolutions of the cylinder in unit time, while a thinner, mobile glue gives correspondingly higher viscosimeter readings. .Thereadings obtained with this standard instrument, in 1% which the glue is maintained at an uniform temperature of 70 F., are given below.
- a small pro o-rtion say from 2 to 10% by weight of a p enolic compound such as carbolic or cresylic acid or the sodium salts of these.
- the amount of petroleum distillate or vegetable oil used may vary from about 1% to 5% by weight of t e glue-base employed, accqrdingto the character of the glue, while that of the phenolic compound may be from 0.1 to 1%. I do not, however, limit myself to these proportions. On an avera e glue, about 2% of the former and 0.2% o the latgive satisfactory re-. sults. As an example of the preferred method of carrying out the inventionthe following-is cited:
- the oily liquid is preferably added to the water before the glue-base, but fairl satisfactory resultsmay be obtained by a ding it to the mixture of glue-base andwater, ust after wetting the glue base, i. e. in the initial stage of the mixing-operation.
- the addition of the oily material (in the same roportion) to the dry glue base, to be en sequently mixed with the water does not appear to give nearly as good results and the addition of the oil to the dry glue base forms no
- the main part of the mixing operation is done after the addition of the oil material.
- a process of abating foamine ss in mix-' ,ing a glue base with water, said glue base containing proteinous material, lime and alkali comprises adding to the water a small percentage of an oil selected from the herein described group consisting of mineral oil distillates and vegetable oils, thereafter adding the glue base to the water and stirring.
- a process of abating foaminess in mixing a glue base with water, said glue base containing proteinous material, lime and alkali which process comprises adding to the water a small percentage of kerosene, thereafteradding the glue base to the water and '3.
- a process of abating foaminess in mixing a glue base with water, said glue base containing proteinous material, lime and-alkali which process comprises'addin to the water a small percentage 01' an o and a The ex- -pression an oil selected from the herein desmall percentage of a phenolic substance as described herein, thereafter adding the glue base to the water and stirring.
- a rocess of abating foaminess in mixing a g ue base with water said glue base containin proteinous material, lime and alkali, whic water a sma 1 percentage of kerosene and a small percentage of cresylic acid, thereafter adding the glue base to the water andv stirrm v 5?
- process of abating foammess in glues which comprises incorporating an oil with the mixing water used with a dry glue base comprisin alkali-soluble proteinous material and ry alkali, such oil being added separatel from the said dry glue base, and being ad d prior to the main part of the operation of mixing said dry glue base with said water to form the li uid glue.
- rocess comprises adding to the
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
Patented Nov. 24,1931
smsinw, or nnmnnmeu, new YORK meme some a GLUES This process has for its object the abatement or prevention of foam 1n glues prepared from proteinous substances such as 1 milk casein, vegetable seed meals and the Itis known thatglues prepared from milk casein by the addition of lime, alkali salts and water, frequently have an undesirable tendency to foam, especially when the dry 'ggingredients have been mixed together and kept in storage for a considerable time or exposed to unfavorable,c0nd1t1ons of temperature and humidity. 3 The foaming tendency exists in such glues, even 1f the casein 35 has previously. been coated with a mineral oil (as has been the pract1ce for many years, for preventing action of the alkaline compounds on. the casein durin storage and shipment. of the .dry glue). lues similarly prepared, from vegetable proteinous sub stances, e. g. peanut meal and other meals of like eharacten frequently show thls tend- ;ency in marked de ree, not only 1n cases wherethe meals or gfues have become stale 1n "as storage but also where fresh meals and chem1- cals aremixed together just before the water is added. Glues prepared from mixtures of milk-casein with one or more of the vegetable seedmeals of commerce may likewise exh1b1t a a tendency to foam. Foam glues, from whatever source, are usually eficient 1n mobility and cohesiveness, do not spread read1ly, and when applied to wood-veneers and the like give inferior joints.
' The resent invention relates to a method of abatmg or preventing the foaming tendency and improving the general character of such glues. It consists in adding to the wet glue (or preferably to the water in which the glue is to be dissolved) an oil WhlCh 1s practically insoluble in water, such as kerosene or other petroleum distillate less volatile than naphtha and lighter than an ordinary motor lubricant, or oil of cedar wood or other suitable oil, preferably together wlth a small amount of a phenolic substance such 'as' phenol, cresol or their sodium compounds, sodium phenate and sodium cresylate. These oils act as foam-abaters, while the phenolic 50 compound acts as a conditioning agent, im-
Application filed ame-a, mo. Serial No. 430,141.
provin the physical character and cohesiveness 0 the glue, and may also be regarded as an auxiliary in the abatement of foam.
In my 00 ending application, Serial No. 372,217 (file June 19,1929) I have disclosed the use of carbon tetrachloride and other chlorinated hydrocarbons for this same purose. There is, however, an important diference between the efiects of carbon tetrachloride and those of the compounds to be described in the present application, viz. its marked thickening action, whereby the viscosity of the glue is increased to an undesirable extent in some cases. I have found that when carbon tetrachloride'is added to protemous glues of the type described above, prepared from milk-casein and/or the seedmeals, a considerable thickening and impairment of mobility is produced, whereas the petroleum distillates and vegetable oils afore- "w said produce no a preciable thickening or I in some cases actua 1y cause a thinning effect which is beneficial for some purposes. As an example of this action the comparative efi'ects of carbon tetrachloride, cottonseed oil, or kerosene used in equal amounts in a given glue are cited below. This is a commercial glue containing about 35% of casein, 35% of peanut meal and appropriate amounts of lime and sodium salts, and is generally mixed with about 2 parts of water to 1- "art of the glue base. For the purpose of t is experiment about 225 parts of cold water are measured into a glue-kettle provided with a mixing device. To this is added 3 parts of the antisfoam substance selected, and the mixer is started. Without interru ting the stirring, 100 parts of the glue powd r are added-and after stirring for twenty minutes the glue y is ready. The consistency of the glue at a this period is determined in'the Stormer viscosimeter, an instrument which consists of a cylinder rotatiu on a vertical axis between. baflies in a cup filled with the glue. The number of rotations per minute is indicated on a dial. A viscous, sluggish glue will show few revolutions of the cylinder in unit time, while a thinner, mobile glue gives correspondingly higher viscosimeter readings. .Thereadings obtained with this standard instrument, in 1% which the glue is maintained at an uniform temperature of 70 F., are given below. Two
sets of readings weremade, the first with the glues at 20 minutes'after wetting and the sec- In this example it will be seen that the viscosimeter readings for the normal glue are 23 and 15; those obtained with the glue in which carbon tetrachloride has been used are much lower, indicating considerable thickening; those with kerosene are substantially higher than normal, indicating thinning,
J ofthe vegetable oils such as cottonseed oil,
ter have been found to while those with cottonseed oil are practically normal.
I have found that the most potent substances in theabatement of foam are those which produce the thinner glues, for example kerosene and the intermediate distillate obtained between the kerosene and li ht lubricating-oil fractions in petroleum re ning, and oil of cedar wood. Efl'ective also are some peanut. oil, coconut oil, and in less degree linseed oil. Of the large number of organic liquids which I have examined, com aratively few have proved to be highly e ective in preventing foam in the casein and seed-meal glues referred to above. Many of them appear to have no anti-foam value. I have selected the substances named above as the'best available at present for this purpose. While these substances maybe used-alone in the manner described, I prefer to add to them a small pro o-rtion, say from 2 to 10% by weight of a p enolic compound such as carbolic or cresylic acid or the sodium salts of these.
The amount of petroleum distillate or vegetable oil used ma vary from about 1% to 5% by weight of t e glue-base employed, accqrdingto the character of the glue, while that of the phenolic compound may be from 0.1 to 1%. I do not, however, limit myself to these proportions. On an avera e glue, about 2% of the former and 0.2% o the latgive satisfactory re-. sults. As an example of the preferred method of carrying out the inventionthe following-is cited:
' E wample I .--100 parts of a glue base consisting of about 40% milk casein, 38% of peanut meal, .11% hydrated, lime, 4% trisodium phosphate and 7% sodium fluoride, were mixed with 225 glue-kettle and stirred by means of a mechanpartof the present invention.
Y stirring.
ounds of cold water in a i'cal agitator for about twenty minutes. The resulting product was a foamy glue of-poor appearance, lacking in fluidity and cohesive-- ness, and in adhesive strength when applied to wood-joints. In another trial, about 2 parts by weight of a 5% solution of cresylic acid in kerosene was mixed into the water before the addition of the glue-base, which was then added and the mixture stirred for twent minutes as before. The glue thus obtaine was much superior in mobility and cohesiveness to that produced from the same glue-base without the addition of the organic liquid, and gave a higher shear strength when applied to ,wood joints. r
The oily liquid is preferably added to the water before the glue-base, but fairl satisfactory resultsmay be obtained by a ding it to the mixture of glue-base andwater, ust after wetting the glue base, i. e. in the initial stage of the mixing-operation. The addition of the oily material (in the same roportion) to the dry glue base, to be en sequently mixed with the water does not appear to give nearly as good results and the addition of the oil to the dry glue base forms no The main part of the mixing operation is done after the addition of the oil material.
It will be understoo that I make no claim herein to the production in general of glues from milk-casein or vegetable seed-meal but only to improvements in the same which result from the abatement or prevention of foam in such glues by the use of one or more of the substances described above.
scribed group consisting of mineral oil distillates and vegetable oils is intended to cover the use of one or several of the oilymaterials mentioned in this specification. No claim, however, is made here to carbon tetrachloride.
I claim 1. A process of abating foamine ss in mix-' ,ing a glue base with water, said glue base containing proteinous material, lime and alkali, which'process comprises adding to the water a small percentage of an oil selected from the herein described group consisting of mineral oil distillates and vegetable oils, thereafter adding the glue base to the water and stirring.
2. A process of abating foaminess in mixing a glue base with water, said glue base containing proteinous material, lime and alkali, which process comprises adding to the water a small percentage of kerosene, thereafteradding the glue base to the water and '3. A process of abating foaminess in mixing a glue base with water, said glue base containing proteinous material, lime and-alkali, which process comprises'addin to the water a small percentage 01' an o and a The ex- -pression an oil selected from the herein desmall percentage of a phenolic substance as described herein, thereafter adding the glue base to the water and stirring.
4. A rocess of abating foaminess in mixing a g ue base with water, said glue base containin proteinous material, lime and alkali, whic water a sma 1 percentage of kerosene and a small percentage of cresylic acid, thereafter adding the glue base to the water andv stirrm v 5? A process of abating foaminess in mixing a glue-base with water, said glue-basecontaming proteinous material, lime and alkali,
which comprises adding to the mix imme-- diately after the initial contact of the gluebase with the water and before any prolonged agitation has taken place, about 1 to 5% of an oil selected from. the herein described group consisting of mineral oil distillates and vegetable oils, and thereafter stirring the mass to form a substantially homo neous, fluid, spreadable glue.
6. process of abating foammess in glues which comprises incorporating an oil with the mixing water used with a dry glue base comprisin alkali-soluble proteinous material and ry alkali, such oil being added separatel from the said dry glue base, and being ad d prior to the main part of the operation of mixing said dry glue base with said water to form the li uid glue.
In testimon whereof aflix mg 51 L WRENCE BRA S ature.
rocess comprises adding to the
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US430141A US1833772A (en) | 1930-02-20 | 1930-02-20 | Abating foaminess in glues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US430141A US1833772A (en) | 1930-02-20 | 1930-02-20 | Abating foaminess in glues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1833772A true US1833772A (en) | 1931-11-24 |
Family
ID=23706220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US430141A Expired - Lifetime US1833772A (en) | 1930-02-20 | 1930-02-20 | Abating foaminess in glues |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1833772A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423214A (en) * | 1944-03-16 | 1947-07-01 | Paper Chemistry Inst | Foam prevention |
| US2475485A (en) * | 1948-12-15 | 1949-07-05 | Oil Well Chemical And Material | Treatment of drilling fluids |
| US2498301A (en) * | 1948-04-07 | 1950-02-21 | Oil Well Chemical & Materials | Treatment of drilling fluids |
| US2751358A (en) * | 1949-11-28 | 1956-06-19 | Shell Dev | Non-foaming detergents |
| US2784106A (en) * | 1955-02-21 | 1957-03-05 | Chicago Mill & Lumber Company | Glue |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
-
1930
- 1930-02-20 US US430141A patent/US1833772A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423214A (en) * | 1944-03-16 | 1947-07-01 | Paper Chemistry Inst | Foam prevention |
| US2498301A (en) * | 1948-04-07 | 1950-02-21 | Oil Well Chemical & Materials | Treatment of drilling fluids |
| US2475485A (en) * | 1948-12-15 | 1949-07-05 | Oil Well Chemical And Material | Treatment of drilling fluids |
| US2751358A (en) * | 1949-11-28 | 1956-06-19 | Shell Dev | Non-foaming detergents |
| US2784106A (en) * | 1955-02-21 | 1957-03-05 | Chicago Mill & Lumber Company | Glue |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
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