'
`
`HEK
`
`H
`
`H
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`HYDRITE EXHIBIT 1027
`
`Hydrite V. Solenis
`Trial IPR2015-1592
`
`(1 of 45)
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`:l
`'I
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`HYDRITE EXHIBIT 1027
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`ATLAS
`SURFACE
`ACTIVE
`AGENTS \
`
`oao
`
`their charucteristics
`. . . the HLB syçterr¡ Pf
`selection , '
`
`Industrìøl Cbemícals Deþørtnent
`ATLAS PO\øDER COMPANY, \TILMINGTON, DELAVARE
`Boston ' Chicago ' Los Angeles ' New York
`'
`In Cønada, address
`ATLAS PO\üøDER COMPANY, CANADA, LIMITED . BRANTFORD, CANADA
`
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`THE COVER
`Illustrated on the cover is a molecular model
`of Tween 20 surface active agent. The color
`division symbolizes'thc affinity of part of the
`molecule for water and part for oil.
`
`copyight 1950, b7
`Atlas Powder ComPany
`Printed io U. S. A.
`
`Arlacel, Arlex, Atlox, Brij, Myrj,
`NNO, Renex, Sorbo, Span, Tween-
`Registered Trademarks of
`Atlas Powder Company
`
`t¡
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`Sugar from corn
`and other farm
`sources.
`
`\':.
`
`,(1.
`
`Beef Fats
`
`ATLAS RESEARCH
`has pioneered in new chemicals
`through CHEMURGY
`
`Atlas research, constantly seeking more and more
`products for consumers at lower costs, has pioneered in
`the science o1 Chemurglt-finding new uses for agricultural
`products through chemistry. One of the new uses is the
`field of surface active agents described in this booklet.
`Traditionally, a major part of Atlas business is the
`manufacture of industrial explosives, made largely from
`raw materials having their origin on the farm. The ex-
`perience of Atlas research chemists over the years
`pointed the way to limitless possibilities for farm materials
`in wholly different industrial uses.
`In the early 1930's, Atlas began turning corn sugar
`into "sugar alcohols", known as mannitol and sorbitol.
`Used nutritionally and medicinally for centuries, they
`had been available only by extraction from fruits and
`berries, and their cost was too high for wide commercial
`adaptation. Through development of low-cost, large-
`scale production, Atlas opened fiesh channels of useful-
`ness for mannitol and sorbitol.
`Most of the emulsifiers, detergents and other types of
`surface active agents described in these pages are derived
`from these "sugar alcohols" through combination with
`various fatty acids of farm, animal or vegetable origin.
`Still others are derived from fatty acid combinations
`w.ith other chemicals. For all its products, Atlas has
`consistently followed a policy of thorough testing-both
`in its own and in independent laboratories-to meet
`exacting standards of dependability.
`The booklet "Chemicals From Farm Products" de-
`scribes the many uses for farm raw materials through Atlas
`Chemurgy. A copy will be sent upon request to Atlas.
`
`Cottonseed Oil
`
`Tall Oil
`
`(t
`
`\
`
`Pork Fats
`
`, .ì'
`
`Sheep Fats
`and Lanolin
`
`,,nill, n
`,l\'/'tl' ',
`
`,,lt
`
`I lr4
`
`Beeswax
`
`i
`
`Soybean Oil
`
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`HOSØ TO USE THIS BOOK
`
`A Key to Other Atlas Literature
`on Surface Active Agents
`
`The pages that follow describe the theory of surface activity, show the characteristics of
`the most commonly used Atlas surface active agents) and give a method of selecting the proper
`agents for certain applications.
`
`To give the industrial user more specific details of practical application in certain industries,
`Atlas publishes supplementary literature on its surface active agents, directed specifically to
`various industrial fields and containing numerous general formulas for compounding of Atlas
`materials into industrial emulsions, cleaners, and other products.
`
`The following is a general list of Atlas publications for users of surface active agents. Any
`or all of these will gladly be sent in answer to a request on your company stationery.
`
`FOR COSMETICS, DRUGS,
`PHARMACEUTICALS, ETC.
`
`Guide to Drug and Cosmetic Emulsion Formu-
`-"4
`lation with Atlas Emulsifrers and llumectants."
`
`FOR DETERGENTS,
`CLEANING COMPOUNDS
`
`-"Non-Ionic Detergents . . for Textile and'Fiber
`Scouring. ..for Compounding...forLaundering."
`
`FOR AGRICULTURAL SPRAYS
`
`FOR TEXTILE PROCESSING
`
`FOR FOODS, PHARMACEUTICALS
`
`t'Atlas Surface Active Agents for Insecticides and
`-
`Herbicides."
`- "Textile Chemicals for Lubricating, Softening,
`Static Control, Sizing, Scouring and Finishing.
`(Sold and Serviced in U. S. by American Viscose
`Corp.)"
`
`-((I{ow Atlas Serves the Food and Pharmaceutical
`Industries with Sorbitol, Mannitol and Ernul-
`sifiers."
`
`Atlas Research and Technical Service Departments will be pleased to cooperate with
`manufacturers who have specific problems not covered in the publications mentioned above.
`
`tv
`
`l l
`
`l.
`
`1ì
`
`:ì
`
`|.
`
`i:
`
`t!
`
`¡l
`
`I
`
`I i
`
`ì
`
`i
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`CONTENTS
`
`Chaþtn 1. Sunr'¡.cB Acrrvrtv eNo Sunrecp Acrrvn AcnNrs
`Definition and Purpose . . . Structure . . . Structure of
`Atlas Surface Active Agents . . . Properties of Surface
`Active Agents
`
`Chaþter 2. Pnopnntrns or Atr-es Sunrecp Acrrvn Aop¡vts
`
`Chaþtcr 3. Cnorcp oF A SuRFAcE AcrrvE AcBNr
`Factors in Selecting an Emulsifier . . ' Procedure in Selec-
`tion of Emulsifiers . . . Procedure in Selection of Surface
`Active Agents for Other PurPoses
`
`P¡,ce,
`
`7
`
`9
`
`15
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`I
`
`Tr
`title page of Chapter 1 illustrates a method
`of visualizing the theory of surface tension by float-
`ing a needle in water.
`The resistance of the surface of the water to rupture
`is actually strong enough to support the weight of
`the needle. In other words, the molecules of the
`water possess sufficient attraction for one another
`at the surface to preVent the needle from falling
`through between them.
`When a surface active agent is added to the water,
`the tension between molecules of water at the sur-
`face is lowered, or relaxed, and the needle sinks.
`
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`Chapter 1
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`CHAPTER 1
`
`SURFACE
`SURFACE
`
`ACTIVITY AND
`ACTIVE AGENTS
`
`Surface active agents are compounds which
`cause variation in the surface forces of a liquid
`in relation to other liquids, gases, or solids. The
`term "surface active agents" is usually applied
`to water-soluble or dispersible materials that
`markedly reduce stllrface tension and interfacial
`tension between tho liquids or a liquid and
`a solid.
`Through use of these agents, it is possible
`to mix dissimilar materials such as oil and
`water, savinþ time and money by decreasing
`the natural réluctance of these materials to
`mix. It is also possible to disperse solids or
`solutions of solids within a liquid, or disperse
`mutually insoluble liquids within another
`liquid. Surface active agents performing such
`functions are known as emulsifiers, dispersing
`agents, or solubilizers. They are widely used
`in the production of food products, pharma-
`ceuticals, cosmetics, textiles, cleaning com-
`pounds, polishes, paints, and agricultural
`er4ulsions.
`1Th.s. same surface phenomena affect the
`ability of liquids to spread out in a thin film
`over Surfaces, or to wet or penetrate surfaces.
`Some surface active agents may be classed as
`
`wetting agents, spreading agents, penetrating
`agents) foaming or antifoaming agents, deter- ,
`gents, or flotation agents, according to their
`final functions. A single surface active agent
`may be effective in more than one application,
`and may perform two or more of these functions
`at the same time. For example, such an agent
`may be used as an emulsifier in a mixture of
`insecticide powder and oily solvent, so that the
`user can add water freely to obtain a homoge-
`neous emulsion. When this emulsion is sprayed
`on plants, the surface active agent may also
`act as a wetting, spreading, or penetrating
`agent,
`Flowever, the requirements for any of these
`uses is varied and divergent, and it is the excep-
`tion rather than the rule when one súrface
`active agent is equally effective in several
`applicatiàns. For example, an emulsifier that
`may be a good detergent for oily rags may not
`be a good emulsifier for the type of., soil on
`the rags. It is this complexity of properties and
`reguirements that demands extensive field
`work rather than a more theoretical approach
`in the application of surface active agents.
`
`Structure of Surface Active Agents
`Chemically, the hydrophilic part of the
`molecule may be, for example, carboxylate,
`sulfate, sulfonate, polyhydric alcohol or alco-
`hol-ether. The lipophilic portion of the mole-
`cule may be a long hvdrocarbon chain. as in
`the fatty acids, or a cyclic hydrocarbon, or a
`combination of the two.
`
`Surface active agents are compounds in
`which one portion of each molecule is hydro-
`philic or water-loving, and another portion is
`lipophilic, or oil-loving. This structure and the
`balance of the two portions of the molecule is
`discussed rrlore fully on page 5, "Properties
`of Surface Active Agents."
`
`2
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`Surface active agents may be classified as
`ionic or non-ionic. The ionic types are either
`anionic or cationic, depending upon whether
`the characteristically surface active portion of
`the compound lies in the anion or cation. In
`soap, the anion (oleate, for example) is the
`effective portion of the molecule and soap is,
`therefore, classified as anionic. Similarly, such
`salts as those of sulfonated oils and sulfated
`alcohols are anionic. Cationic surface active
`agents, such as cetyl pyridinium sulfate, or the
`morpholinium alkyl sulfates, on the other
`hand, comprise a complex polar cation asso-
`ciated with an inorganic anion.
`In an ionic surface active agent, the hydro-
`philic portion of the molecule is frequently
`weak. Its attraction to water may be increased
`by combination with an inorganic ion. Soap,
`for example, consists of an oil soluble fatty acid
`chain with a polar carboxyl group whose
`water attraction is enhanced by neutraliza-
`tion with an alkali. Due to its ionic character,
`it is sensitive to the presence of other ions.
`Thus, soaps are ineffective in hard water
`and in electrolytes. Antagonistic surface
`active agents also illustrate such sensitivity.
`Non-ionic surface active agents depend
`
`chiefly upon hydroxyl groups and ether link-
`ages (from polyhydric alcohol anhydrides and
`polyoxyethylene chains) to create the hydro-
`philic action. Since they do not ionize, thcy
`are comparatively insensitive to hard water
`and electrolytes.
`STRUCTURE OF ATTAS
`SURFACE ACTIVE AGENTS
`Atlas non-ionic surface active agents are
`complex esters and ester-ethers, their chemical
`starting point being hexahydric alcohols, alky-
`lene oxide, fatty acids and fatty alcohols. The
`hydrophile character of these surface active
`agents is supplied by free hydroxyl and oxy-
`ethylene groups, while the lipophile portion is
`found in the long hydrocarbon chain of the
`fatty acids or fatty alcohols.
`Typical of the Atlas surface active agents
`are the Span, Arlacel and Tween products.
`The Span type materials are essentially partial
`esters of the common fatty acids (lauric,
`palmitic, stearic, and oleic) and hexitol an-
`hydrides (hexitans and hexides), derived from
`sorbitol. The structure of the monoester Span
`products is illustrated in Figure 1.
`HEXITOL HEXITANS and HEXIDES
`o
`
`-H'o
`
`CHt
`
`cH-cH,-ol{
`
`CH,
`
`cH - cHroocR
`
`SP,A.N or ARLACEL
`o
`
`cHr- oH
`I
`HC-OH
`
`I
`
`HO-CH
`
`I
`
`HC -OH
`I
`HC-OH
`Hr-oH
`SORBITOL
`
`Ic
`
`HO-CH
`
`CH-OH
`
`CH-OH
`
`HO -CH
`
`CH -OH
`
`CHt
`
`cH-cH-cHroocR
`
`CH.
`
`cH - oocR
`
`IO
`
`H
`
`o
`
`o
`
`o
`
`OH
`
`I C
`
`H
`
`CH,
`
`R=the residue of o long choin forty ocid
`
`3
`
`HO-CH
`
`CH-OH
`
`CH-OH
`
`HO-CH
`
`CH-OH
`
`Figure l-Configura-
`tional formulas for
`the components of a
`typical Span, whose
`formation involves
`anhydrization to hex-
`itans and hexides and
`their esterification.
`
`cH-cH-cH,
`OH OH
`
`---++HOOCR
`
`CHt
`
`o
`-HrO I
`
`HO-CH
`
`CH,
`
`o
`
`CH'
`
`CH-OH
`
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`

`The Arlacel emulsifiers, which are made
`especially for cosmetic and pharmaceutical
`use, are similar to the Span products in
`chemicol composition. They are prepared by
`further treating the Span materials to obtain a
`very light color. The Span and Arlacel products
`of like number correspond chemically, i. e.,
`Span 20 is similar chemically to Arlacel 20. *
`The Tween type materials are derived from
`the Span products by adding polyoxyethylene
`chains to the non-esterified hydroxyls. Both
`types are actually complex mixtures of several
`compounds. Typical Tween compositions are
`shown in Figure 2.
`The Myrj products represent a different
`structure in which no hexahydric alcohol is
`present. As seen in Figure 3, the fatty acid
`and the alkylene oxide react directly to form
`an ester-ether of the desired properties.
`The Brij products, illustrated in Figure 4,
`contain no ester linkages. This differentiates
`them from the Myrj products to which they at
`first appear similar. The fact that ether groups
`
`*Arlacel C (see description Table I following page 10) is a
`general-puipose emulsifier and corresponds chemically to
`Ãrlacel 83 of the cosmetic series.
`
`alone are present provides high resistance to
`alkaline conditions.
`Still another type of Atlas non-ionic agent
`is depicted in Figure 5. Here the'hexitol and
`the alkylene oxide are first reacted, then this
`produci is esterified. Some of the Atlox prod-
`ucts are of this chemical structure.
`An almost unlimited number of products is
`complex esters and ester-ethers, their chemical
`therefore possible for Atlas to "tailor make"
`specific agents of high efficiency for major
`applications.
`The chemical versatility of the b4se mole-
`cule in these surface active agents permits
`numerous types and variations of material to
`suit different oil-water conditions. For ex-
`ample, the Span products tend to be oil-
`soluble, but dispersible or insoluble in water,
`while the Tween products, generally speaking,
`are soluble or dispersible in water. The Myrj
`and Brij types of surface active agents are
`similar in solubility to the Tween type mate-
`rials. The polyoxyethylene sorbitol fatty acid
`ester type can range from as lipophilic and as
`oil-soluble as the Spans, to as hydrophilic and
`water-soluble as the Tweens.
`
`SPAN
`
`o
`
`CHz
`
`CH - CH¡OOCR
`
`HO-CH
`
`CH-OH
`
`CH-OH
`
`HO-CH
`
`CH-OH
`
`CH¿
`
`CH-CH-CH¿OOCR
`
`I
`
`OH
`
`HH
`+¡'N'r Hc_cH\/o
`----------|
`
`Figure 2-Show-
`ing derivation of
`Tween fromSpan
`by addition of
`polyoxyethylene
`chains,
`
`FA.TTY ACID
`Figure 3-Myrj
`products are
`made by dire.ct
`reaction of fatty
`acid with alkyl-
`ene oxide.
`
`F'"!
`
`4
`
`T\üøEEN
`
`o
`
`CH¿
`
`CH - CH¿OOCR
`
`H (O-CH¡-CHd-O-CH
`n!
`
`CH-O-(CHr-CHz-O)-H
`
`H-(O-CH¡-CHz)-O-CH
`NI
`
`CH-O-(CHz-CHz-O)-H
`n2
`CH - O(cH¿- CH¿ - O) - H
`n2
`
`CHz
`
`CH-CH-CHTOOCR
`
`o
`nr+ n2+ nJ: ¡rN"
`
`Io(cHr-
`
`CH¿-O)-H
`nt
`
`MYRJ
`
`tr CHz- CH¿ - O - (CHz- CHz - O -,.rr-.r, - Oi-.l
`
`N-2 __l
`
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`

`FATTY ALCOHOL
`Figure 4-Show-
`ing derivation of
`Brij products by
`additionof alkyl-
`ene oxide to fatty
`alcohol.
`
`E"l
`
`BRIJ
`
`CH¿-CH¿ - o - (CHu-CHr- O - )fiHr;cHr -
`
`HEXITOL POLYOXYETHYLENE HEXITOL
`
`ESTER
`
`CH¡-O(CHr- CH¡-O)CHr- CHr- OOCR
`,t - o(.r,-.r,- oll'- t
`I
`n,
`-CHI)O - CHn'rt
`- o(ar,- ar,- o),
`Hl- o(ct¡,'cxr- o)f'
`år,-o(.r,-.r,-3ít
`
`nr+n1+n3+n..rn5f n6: rrNil
`
`+"N"
`
`HH
`HC-CH
`o
`
`------t>
`
`CH¡ - OH
`IHC-OH
`I-cH
`IHC-OH
`IHC- OH
`Hz - OH
`
`IC
`
`HO
`
`Figure S-Showing
`derivation of poly-
`oxyethylene hexitol
`ester (such as Atlox
`products).
`
`Properties of Surface Active Agents
`
`How usefiil will a certain surface active
`agent be in a given field of use? The answer
`to this question appears to be chiefly in two
`major properties and only slightly in the
`many "standard" physical properties. The
`two major properties are: hydrophile-lipophile
`balance (HLB) and chemical identity.
`
`HLB value. In the next example, Tween 80,
`the accumulation of polyoxyethylene chains on
`the hexitan residue renders this part of the
`rirolecule sufficiently hydrophilic (high HLB)
`to drag the oleic acid chain completely into
`the water layer. The third example, Tween 81,
`is an intermediate tYPe.
`
`OIL LAYER
`
`HYDROPHILE.LIPOPHILE
`BATANCE
`The term ((HLB" indicates the size and
`strength of the hydrophilic and lipophilic
`groups that form the molecule of the surface
`active agent.
`The accompanying sketch (Figure 6) repre-
`sents the behavior of Atlas surface active agents
`at an oil-water interface. All three are oleic de-
`rivatives. The hexitan residue in Span 80 is
`not sufficiently water-loving, or hydrophilic,
`to draw the oilJoving or lipophilic oleic acid
`chain into the water layer' Span B0 has a low
`
`coo
`
`OX OH
`SPAN 80
`
`coo)-o
`
`oìo"
`
`TWEEN 80
`
`\o
`
`o
`
`^oÇvoo
`ç
`,"
`oè
`t"or-o
`ho"
`WATER LAYER
`Fig. 6
`
`. o_
`
`o
`
`coo
`
`è'oì"lv
`
`HO
`
`t?:
`l"i ,
`
`o
`
`I-
`
`eo
`
`Hoaox
`OH
`TWEEN 81
`
`5
`
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`

`CHEMICAT IDENTITY
`Chemical identity of a non-ionic surface
`active agent refers to its overall chemical
`structure, whether an ester, ether, mono ot di
`ester, etc. This identity and HLB appear to be
`the two prime considerations in the selection
`of a surface active agent.
`
`SOTUBITITY
`The solubility of a surface active agent is
`of interest for two reasons. Limited solubility
`of a compound usually fosters surface activity.
`The application frequen tly demands that the
`product be water soluble, or soluble in a given
`oil, solvent, or wax mixture. When the agent
`is not soluble to the desired extent, a coupling
`agent or mutual solvent is added to attain
`solubility.
`
`SURFACE TENSION
`A surface active material is generally less
`soluble than a non-surface active material and
`this property promotes its collection at
`any interface, gas-liquid, liquid-liquid or
`liquid-solid. Collection of the material at an
`interface is observed as a drop in surface or
`interfacial tension. These properties may be
`measured and as such are an indication of
`surface activity. The work involved in this
`collection at an interface is related to the sur-
`face tension reduction of the solution.
`The force of surface tension in liquids evi-
`dences itself in the attraction between mole-
`cules of the liquid at its surface, and the
`measurement of surface tension is the work
`required to break or counteract this attraction.
`A popular method of measuring this is the ring
`method, using the DuNouy Tensiometer, in
`which a suspended platinum ring is lifted out
`of the liquid from a position of rest at the im-
`mediate surface. A reading of surface tension,
`in dynes per centiméter, is obtained by noting
`the force required to pull the ring through the
`air-water interface. A surface active agent,
`
`6
`
`I
`
`Fig. 7-surface tension measurement by DuNouy Tensi-
`omeier. Surfaci tension is the force, in dynes per centimeter,
`required to lift the suspended platinum ring out of the liquid
`from a position of rest at the immediate surface.
`
`by reducing the force required to break the
`surface, lowers tension values.
`
`INTERFACIAT TENSION
`While surface tension measurements usually
`deal with the force required to break the sur-
`face between liquid and air, measurements of
`interfacial tension generally express the force
`necessary to break the interface between im-
`'miscible liquids, such as oil and water.
`The DuNouy Tensiometer is used in much
`the same way as for the surface tension de-
`termination. In this case, a layer of oil is
`carefully placed on the aqueous layer to form
`an interface, through which the ring is pulled.
`Interfacial tension is also expressed in dynes
`per centimeter. Here again, the addition of
`
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`

`agent in this respect. Ffowever, interfacial
`tension is not necessarily an indication of how
`well the oil and water will remain mixed.
`The conditions under which measurements
`are made are artificial and do not exist in a
`finished emulsion. There the surface active
`agent will usually be distributed through both
`the water and the oil phases of the mixture,
`instead of in the water only as in the standard
`method of measurement. For this rcason,
`further studies of interfacial tension with the
`surface active agent dissolved in the oil phase,
`or with one or more agents dispersed equally
`in the water and oil phases, are frequcntly of
`assistance in forecasting emulsion stability.
`Of course, such stability is also dependent
`upon such other factors as the difference be_
`tween the densities of the two phases, and
`conditions of storage.
`
`SPREADING COEFFICIENT
`
`Spreading coefficient is a measure of the
`tendency of a liquid to spread over a surface,
`either liquid or solid. It is equal to the surface
`tension of the reference oil minus the sum of
`the surface tension of the solution or dispersion
`(of the surface active agent in water) and the
`measured interfacial tension (between the solu_
`tion and the reference oil).
`S' C' : S'T'ol'- (S'T'.orurio, * I.'I.oil7.o1u¡¡o.)
`Usuallythe measurementsrepresent thespread-
`ing coefficients of the surface active solution
`
`Fig, B-Interfacial tension measurement. Oii is layered
`over water, in which the ring is immersed, Measurements
`are made of the force required to lift the ring through the oil_
`water interface
`
`a surface active agent reduces the force re-
`quired to break through the interface.
`In general, the lower the interfacial tension
`induced by the emulsifier, the easier it is to
`get the oil and water to mix. The closer these
`values approach zero, the more effective is the
`
`qG_
`
`<>
`
`.-
`-
`
`..>
`
`Fig, 9-Illustrating effect of a surface active agent on the
`spreading properties of a liquid. At left are globules of water
`standing on waxed surface of a pane of glass. (Parallel lines
`
`across bottom of photo are edges of pane.) At right are water
`globules to which surface active agent has been addecl, on
`same surface. Note how water spreads out in thin film.
`
`7
`
`:,
`
`.T
`
`';
`
`:!
`?,
`
`I j
`
`'l
`þt-
`
`Ë'
`
`)ägi
`
`ls¡
`
`t
`IEíl
`
`qi
`
`i $r
`
`t\ i
`
`tÊ n
`
`¿&H
`
`.ra\lÍ
`
`# bI f
`
`t
`
`t!;iI
`
`¡t
`'èi
`rf
`;l
`i{
`
`{r
`
`i
`i::
`
`å 2
`
`'a
`
`'
`
`!
`
`L
`
`HYDRITE EXHIBIT 1027
`Hydrite v. Solenis
`Trial IPR2015-1592
`(14 of 45)
`
`

`

`on Nujol. * The greater the spreading coeffi-
`cient (more positive), the greater the wetting
`and spreading power (Cupples,I.E.C.n,l2I9
`(1e35) ).
`
`MIGRATION TO INTERFACE
`The collection of a surface active agent at
`an interface occurs in a relatively short, but
`finite, time. This action is noted by a drop
`in surface tension with time.** Surface and
`interfacial tension measurements are usually
`made and reported under static conditions,
`i.e., after collection has occurred and the read-
`ing has reached a constant value.
`
`PARTICLE CHARGE
`By definition, ionic surface active agents
`exhibit a particle charge whereas non-ionic
`agents have none. Generally, non-ionic agents
`may be more widely used because of lack of
`antagonistic effect of electrolytes and surface
`active agents.
`
`*A high viscosity, USP mineral oil sold under the trademark
`"Nujol" by Stanco, Inc,
`*rYoungand Coons, Surface Active Agents, 45,7945,Chem-
`ical Publishing Company.
`
`CHEMICAL REACTIVITY
`Usually a lack of chemical reactivity or an
`inert character is desired in a surface active
`agent. Otherwise the agent may be destroyed,
`with resultant loss in emulsification, wetting,
`detergent value, etc., or a major component
`of the system may be affected.
`An example of this latter effect occurs with
`the addition of soaps to quaternary ammonium
`"cold sterilizers." The fatty acid ion of the
`soap reacts with the quaternary ammonium
`compound and reduces its germicidal effect.
`
`EDIBITITY
`In general, non-ionic surface active agents
`are less toxic, less irritating, and therefore
`more suitable for foods, pharmaceuticals, cos-
`metics, and other high-quality applications
`than ionic types. Many Atlas products have
`been subjected to extensive feeding studies and
`ôopies of these data and reference.s are avail-
`able from Atlas.
`
`T;t Chapter 2 frontispiece (opposite page) shows
`the Cenco DuNouy Tensiometer with which surface
`tension and interfacial tension measurements are
`made at Atlas' Central Research Laboratory near
`Wilmington, Del. The use of this instrument is more
`fully described on page 6. The specially built case
`in the accompanying photo permits more precise
`measurements.
`
`8
`
`HYDRITE EXHIBIT 1027
`Hydrite v. Solenis
`Trial IPR2015-1592
`(15 of 45)
`
`

`

`Chapter 2
`
`HYDRITE EXHIBIT 1027
`Hydrite v. Solenis
`Trial IPR2015-1592
`(16 of 45)
`
`

`

`CHAPTER 2
`
`PROPERTIES OF ATLAS
`SURFACE ACTIVE AGENTS
`
`Atlas surface active agents referred to in this
`manual are non-ionic complex mixtures bear-
`ing the chemical designation of the simple ester
`or- esters to which the composition as a whole
`most nearly corresponds with respect to analyt-
`ical constants, particularly hydroxyl number
`and saponification values. These agents are
`non-electrolytes. They are neither sulfates nor
`sulfonated products, and contain practically no
`soap, free fatty acids or inorganic salts.
`
`HYDROPHILE-LIPOPHILE
`BALANCE (See Tables I and II)
`An empirical number has been given each
`Atlas surface active agent, representing its hy-
`drophile-lipophile balance (HLB). By compar-
`ing these numbers in Tables I and II with
`Table VI on page 24, the technician finds a
`simple guide to the use of these agents in spe-
`cific applications.
`The lower the HLB value, the more lipo-
`philic (oil-toving) is the material, and con-
`versely, the higher the HLB value, the more
`hydrophilic (water-loving) is the material. In
`general, the Span type of product is therefore
`Iipophilic and most of the Tween type are
`hydrophilic. Those in the HLB range of 10
`-1 1 are intermediate.
`lo
`
`PHYSICAL CHARACTERISTICS
`(See Tables I and II)
`Atlas surface active agents are supplied in
`97/s to 10070 concentration unless otherwise
`designated. They are virtually neutral' They
`are non-volatile and heat stable. They range
`from thin liquids through viscous oils to soft
`and hard waxes.
`
`SOLUBITITY AND
`GENERAL CHARACTERISTICS
`(See Tables I and II)
`Atlas surface active agents offer a wide range
`of solubility-from oil-solubility to water-solu-
`bility, with many gradations of organic solu-
`bility. An important factor in their practical
`application is that they are miscible with one
`another. In addition, they provide almost
`universal compatibility with materials to be
`emulsified.
`The Tween products and other polyoxyeth-
`ylene derivatives are generally soluble or dis-
`persible in water, and differ widely in organic
`solubilities. The Span products, NNO and
`other hexitan clerivatives of fatty acids are
`generally insoluble or dispersible in water and
`soluble in most organic solvents.
`
`HYDRITE EXHIBIT 1027
`Hydrite v. Solenis
`Trial IPR2015-1592
`(17 of 45)
`
`

`

`Table No. I
`
`GENERAL CHARACTERISTICS OF ATLAS NON-IONIC SURFACE ACTIVE AGENTS
`
`Table No_ 1
`
` Cello-
`
`
`
`
`
`NON-AQUEOUS SOL.
`
`SOLUBILITY AT 25° C.
`
`
`
`
`
`
`
`Viscosity
`
`(CF.at25°C)
`
`
`
`
`Sorbitan monostearate .
`
`Sorbitan tristearate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`,
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`Sorbitan monooleate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`
`
`Sorbitan trioleate .
`
`.
`
`.
`
`.
`
`Sorbitan sesquioleate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`Glycerol sorbitan laurate .
`
`.
`
`.
`
`Arlacel C
`
`Tween 20
`
`Polyoxyethylene sorbitan monolaurate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`
`
`
`
`-6
`
`
`
`Lemon-Orange
`
`
`55
`
`
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`Specific
`
`Gravity
`
`Carbon
`.
`,
`Ace-
`Corn
`Diethyl Dioxan
`
`Tetra-
`Md‘? 1
`
`Ether
`tone
`Oil
`
`
`solve
`chloride
`SP”'“5
`
` 1.00v1.06
`8.6
`Sorbitan monolaurate .
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`Red Amber
`SC
`Oily Liquid
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
` Sorbitan monopalmitate . . . . . . . . . . . . . . . . . . . . . .
`
`1.00-1.05
`Tan
`6.7 Waxy Solid
`
`
`Sorbitan monostearate .
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`
`
`4.7 Waxy Solid
`0.98-1.03
`Light Cream
`
`5.9
`O.95~1.10
`Light Cream
`Waxy Solid
`
`
`
`0.95-1.00
`Cream
`
`A 2.1 waxy Solid
`
`
`
`
`Amber
`1.00-1.05
`410
`475
`4.3 Oily Liquid
`
`
`
`
`
`
`
`570
`Amber
`
`00 A
`1.3 Thin Oily Liquid
`100— 250
`0.92098
`
`50
`3 4
`::
`Oily Liquid
`250- 400
`1.0a—1.13
`610
`
`
`350- 550
`.
`Oily Liquid
`1.05-1.10
`410
`
`
`
`. Oily Liquid**
`400- 600
`1.05-1.10
`630
`655 Lemon-Orange
`400— 600
`1.05-1.10
`545
`.
`.
`.
`.
`.
`635 Lemon-Orange
`Oily Liquid * *
`
`l.04~1.08
`Yellow
`Waxy Solid
`
`
`
`DG
`.
`Waxy Solid
`1.03—-1.08
`Light Yellow
`
`S
`.
`15.0 Oily Liquid
`1,064.10
`Lemon
`
`D
`Oily Liquid**
`1.00-1.05
`Leriioiiii
`A
`.
`
`
`
`D
`.
`Oily Liquid**
`1.00-1.05
`1.08-1.12
`Oily Liquid
`1.08-1.13
`
`.
`Polyoxyethylene sorbitan trislearate .
`Tween 65
`.
`Polyoxyethylcnc sorbitan monooleate .
`Tween 80
`
`.
`Tween 81
`Polyoxyethylene sorbitan monooleate .
`
`.
`Tween 85
`Polyoxyethylene sorbitan triolcate .
`.
`.
`.
`Polyoxyethylene sorbitan monolaurate .
`G-7596-J
`G-7596-P
`G-7076-H
`
`Polyoxyethylene sorbitan monolaurate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`
`
`Polyoxyethylene sorbitan dilaurate .
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`..
`
`.
`
`.
`
`.
`
`Oily Liquid
`
`1.02-1.07
`
`SC
`
`SC
`
`S
`
`Polyoxyethylene sorbitan monolaurate .
`
`.
`
`.
`
`.
`
`Polyoxyethylene sorbitan monopalmitatc .
`
`Polyoxyethylene sorbitan monostearate. .
`
`Polyoxyethylene sorbitan monostearate .
`
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`.
`
`
`
`Tween 2 1
`
`
`Tween 40
`
`Tween 60
`
`
`
`Tween 61
`
`
`
`Tween 61
`
`Tween 65
`
`Tween 30
`
`Tween 81
`
`
`
`Tween 85
`
`
`
`
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`.
`.
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`.
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`.
`.
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`.
`.
`.
`
`.
`
`.
`.
`.
`.
`
`.
`.
`.
`.
`
`.
`.
`.
`.
`
`.
`
`.
`.
`.
`.
`.
`
`.
`
`Oily Liquid
`
`.
`
`.
`
`.
`
`
`
`ac/immm
`
`EC/JC/ICIJC/J(lJ(IJU)(I)UJ(I)(flE/II/if/J
`
`Cl)
`
`
`
`s
`s
`
`s
`s
`
`1
`1
`
`I
`1
`
`I
`I
`
`
`
`1
`I
`
`S=Soluble; SS=Slightly Soluble; SW=Soluble Warm (50° (3.); S(H) =Solublc, but Hazy; SC=Soluble at High Concentrations;
`D =Dispersible; DW= Dispcrsiblc Warm (50° C.); I = Insoluble; * =Saponifies on Standing; ‘]'=lnsoluble at certain concentrations;
`G=Gels at High Concentrations.
`
`HYDRITE EXHIBIT 1027
`
`Hydrite V. Solenis
`Trial lPR2015-1592
`
`(18 of45)
`
`
`
`
`
`
`
`1.05~1.10
`Oily Liquid
`I
`ST
`S
`ST
`ST
`
`
`
` I 1.05-1.10
`—'_
`s
`s
`
` I ST
`1.00-1.05
`VVaxy Semi-Solid
`1
`s
`S(H)
`S(H)
`S(H)
`S(H)
`
`1.08-1.13
`M/axy Solid
`I
`so
`ST
`D
`I
`ss
`ss
`
`
`
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
` Waxy Solid
`s
`-
`s
`s
`s
`I
`I
`
`. I Waxy Solid
`s
`s
`s
`s
`I
`s
`
`
`—
`—
`—
`I
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`Waxy Solid
`
`s
`s
`s
`s
`S(H)
`s
`s
`I
`1
`S(H)
`S(H)
`=-I-
`“Tends to gel on standing
`
`
`
`
`
`Oily Liquid
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`.
`.
`
`.
`
`.
`
`Polyoxyethylene sorbitan monopalmitate .
`Polyoxyethylene sorbitan monooleate .
`.
`.
`.
`
`
`
`
`
`G-7426-N
` G-9446-N
`
`Polyoxyethylene stearate . .
` Polyoxyethylene stearate .
`.
` Polyoxyethylene stearate .
` Polyoxyethylenc stearate. .
`
`Polyoxyethylene stearate .
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`. .
`
`.
`
`.
`
`.
`
`.
`
`
`
`HYDRITE EXHIBIT 1027
`Hydrite v. Solenis
`Trial IPR2015-1592
`(18 of 45)
`
`

`

`Table No. II
`
`GENERAL CHARACTERISTICS OF ATLAS NON-IONIC SURFACE ACTIVE AGENTS
`
`Table No. H
`
`Name
`
`G-1061
`
`
`
`D S
`
`Compound
`
`Viscosity
`
`Form at 25“ C. (cP_ at zsac‘)
`
`(T=“é.‘;
`
`HLB
`
`SOLUBILITY AT 25° C.
`AQUEOUS SOL.
`
`
`Cotton-
`seed
`
`Corn
`
`NON-AQUEOUS SOL.
`
`Ace-
`
`Diethyl
`
`.
`
`Cell
`
`.
`
`HSO
`
`NIOH
`
`Na SO
`
`AICI,
`
`Min'l
`
`Polyoxyethylerle sorbitol monolaurate .
`Polyoxyethylene sorbitol pentalaurate .
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`Oily Liquid
`
`1000-1500
`
`7 5- 200
`
`1.os—1.13
`0.98-1.03
`
`D
`
`SS
`SC
`
`D
`I
`
`D
`I
`
`D
`
`D
`s n
`S
`S
`
`I
`
`S
`
`S
`
`SS
`
`S
`
`S
`
`
`
`Polyoxyethylene sorbitol hexastearate .
`Polyoxyethylene sorbitol tetraoleate .
`. .
`
`.
`
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`.
`
`.
`
`.
`
`.
`
`,
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`.
`
`Oily Liquid
`
`Waxy Solid
`
`Oily Liquid
`
`
`
`0.92-0.98
`
`0.92-0.98
`
`0.95-1.00
`
`051 U)
`
`SX
`
`SWX
`
`SWX
`
`STX
`
`s
`sx
`
`s
`swx
`
`so
`
`s
`si
`sx
`
`. s
`s
`scwx scwx
`
`SX
`
`so
`
`D
`D
`
`s
`s
`
`300
`
`450
`
`
`HECDUJUJUJ
`{AmiHHHI/IUJUJUJ H
`
`I T
`@ Di H
`
`lIE
`‘PN WOO
`
`S
`
`S
`
`S
`
`S
`
`Atlox 1045
`
`Atlox 1045-A
`
`s s
`
`S
`
`S
`
`S
`
`S
`
`S
`
`0.92%).98
`200
`Oily Liquid
`
`50
`--
`Oily Liquid
`100- 2
`0.98-1.03
`470
`550
`
`
`100- 200 _ 0.92-0.98 — Light Lemon n I
`1200-1400 - 0.92-1.02“
`100- 200
`1.00-1.05
`440
`525
`Light Yellow S(H)G S(I-i)G
`150- 250
`1.00-1.05
`475
`560
`Yellow
`D
`D
`
`Oily Liquid
`.
`. H Oily Liquid
`.
`11.5 Oily Liquid
`13.2 Oily Liquid
`
`.
`
`DG
`
`S(H)G
`
`DW*
`
`U:Q
`
`DG
`D
`
`SH)
`U)
`
`ICOC/Jfllf/2
`
`H
`(AU)
`U1
`
`IUJCDEIJU2
`
`S
`
`S
`
`S
`
`S
`
`S
`
`S
`
`Polyoxyethylene sorbitol cottonseed oil derivative .
`Polyoxypropylene mannitol dioleate .
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`.
`Po