JPH02500190A - Poly(alkylene carbonate) polyal having an average of one or less acid terminal components and its salts - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Poly(alkylene carbonate) polyal having an average of less than one acid end component and its basic invention is a polymer containing a poly(alkylene carbonate) main chain ( (including oligomers).

Poly(alkylene carbonate) polyal is a combination of an alkylene carbonate component and and ether components such as di- and higher polyalkyleneoxy units. It is a dumbed polymer. Alkylene carbonate component is bonded to carbonate component It is a repeating unit containing an alkylene group. Known poly(alkyleneka) -bonate) Some polyals are nonionic surfactants.

In 1978, 5tuehler added a curl to the main chain in DB 2,712.162. Nonionic surfactants containing bonate are disclosed. According to Langdon et al. Many surfactants have been manufactured and described in many patents, including U.S. Patent No. 4.0. 72.704 is either dialkyl carbonate or formaldehyde Coupling with polyethylene glycol and polypropylene glycol, It is described that materials with surface-active properties are obtained. Hydrophilic using US patent le It has been described that it can be combined with polyglycols to obtain surface-active properties. This job is rice In National Patent No. 4.504.418, polyoxyalkylene polymers and Functionalized aliphatic, aromatic or aliphatic-aromatic alcohols with alkyl carbonates esters of dicarboxylic acids or dicarboxylic acids to obtain substances with surface-active properties. expanded to include

U.S. Pat. No. 4,330,481 to Timberlake et al. is produced by reacting alcohol ethoxylate with ethylene carbonate. Describes the production of surfactants. As reported in U.S. Patent No. 4,415,502 This product is further reacted with ethylene oxide to form different surface-active compounds. Manufactured with quality. Alcohol, phenol or carboxylic acid (or alkylene carbonate or alkylene oxide and Production of surfactants and functional fluids by reacting with carbon oxide is Cu5cur ida, US Pat. No. 4,488,982.

U.S. Pat. No. 4,382,014 to 5akai et al. (-ate ) Alcohols containing 4 or more carbon atoms or substituted phenols in the presence of complexes , reacting a carboxylic acid or a primary or secondary amine with an alkylene carbonate. describes the production of surface-active substances by

Low molecular weight polyoxy Ethylene glycol monomethyl ether is phosgene or alkyl carbonate Substances that are combined with and are useful in the formulation of brake fluids and as synthetic lubricants. I got it.

Monofunctional alcohols using diphenyl carbonate to obtain surfactants, Coupling of phenols or ethoxylated derivatives thereof is described in U.S. Pat. No. 3,332,980. Disclosed in the issue.

U.S. Patent No. 4,267, 120 to Cucurida and Peranza et al. No. is a cyclic organic acid anhydride, 1,2-epoxide, carbon dioxide in the presence of a basic catalyst. and a new polyester polycarbon obtained by reacting polyhydric compounds. Nate is listed. The resulting polyester polycarbonate has hydroxy groups terminal group and is not an acid functional substance or a surfactant.

This nonionic surfactant has the potential to be degraded by bases, strong acids, or under biodegradable conditions. -bonate backbone. This destabilizes this surfactant as it does not persist in the environment. and make it principally compatible. Unfortunately, this nonionic poly(alkylene carbonate) g) Polyal surfactants have limited applications due to their poor water solubility and wetting time. It is.

Furthermore, this nonionic surfactant forms a form with poor form stability. , which can be advantageous or disadvantageous depending on the particular application. Also, a table such as the surface tension of water Fairly high concentrations of this nonionic surfactant are required prior to its surface-active properties.

Regarding this drawback of poly(alkylene carbonate) polyal surfactants, water For biodegradable surfactants with insoluble components that can be dispersed and/or solubilized in There is a request to do so.

- In embodiments, the invention provides for fewer (both 0.05 and less than 1 parent per molecule) A novel acid-functional poly(alkylene carbonate) polyal with aqueous ends. Ru. The hydrophilic end is preferably an acidic moiety, such as -COOH, -SO□H, 5Os H, 5oak.

-PO, H, or -POJz or sulfosuccinate.

Salts of this polyal, such as alkali metals, alkaline earth metals, ammonium and amine salts are also included in this acidic functional group.

In another embodiment of the invention, at least one monofunctional alcohol, mercapta primary or secondary amines or carboxylic acids, C5-24 alkyl substituted phenols or an adduct of its ethoxylate and (1) alkylene carbonate, ( 2) Alkylene oxide and CO□, (3) Alkylene oxide, alkylene carbonate carbon dioxide, and (4) poly(alkylene carbonate) polyar selected from the group consisting of Polymers comprising a reaction product of a substance capable of reacting with said adduct to add groups. (alkylene carbonate) polyal is provided. This composition has surface active properties. have sex.

The present invention also provides random poly(alkylene carbonate) oxides in the form of salts with terminal acid groups. Provides salts of oligomers and polymers. This polyal salt also has surface-active properties. have

In another embodiment B of the present invention, a novel acid-functional poly(alkylene carbonate) polyester and its salts, which by themselves or with additional non-ionic or may be used in combination with anionic surfactants or their salts. stomach.

The novel compositions of the present invention have the advantageous surfactant properties of nonionic surfactants and It combines the improved properties obtained from functional surfactants. In this composition, the po Combination of poly(alkylene carbonate) polyal main chain and terminal acid functional components makes an excellent surfactant. This new composition is obtained from current surfactants May be used at much lower concentrations than nonionic polymers, saving material and cost give sufficient economic advantages in terms of This new composition also has a shows an increase in water solubility when compared to The excellent properties of this new polyal are due to its surface activity. Enables new uses of sexual agents and their easy handling. Furthermore, the negative aspects of the present invention The increased surface activity and water solubility of ionic polymers compared to nonionic polymers Wetting time decreases. Furthermore, the polymer of the present invention is a nonionic poly(alkylene carcinogen). (bonate) gives higher foam height and foam stability than polyal.

One particularly advantageous property of the surfactants of the present invention is that poly(alkylene carbonate) ) polyal, polyether polyal and polyester polyal (products such as Ability to form quality stable or easily dispersible water-based emulsions or dispersions It is power. The dispersions and emulsions have a low viscosity which considerably facilitates the handling of this material. Provides a system that can be inhaled and discharged at different times.

Poly(alkylene carbonate) poly used in the production of the novel polymer of the present invention R is a random component containing a large number of carbonate components and a large number of active hydrogen components. It is a chemical polymer.

The alkylene carbonate component has an alkylene group bonded to the carbonate component. It is a repeating unit. An active hydrogen component is a component that contains hydrogen atoms; Kohler et al. J, Amer, Cheap, S oc, 49:318H1927). It shows significant activity.

Examples of such hydrogen components suitable for the preparation of the polymers of the invention include aliphatic, cycloaliphatic, Aryl, alkylaryl, aralkyl and polyalkyleneoxy-functional Hydrolic alcohols, mercaptans, amides, carboxylic acids, primary and secondary amines and are alkyl-substituted phenols and their ethoxylates. alkyleneoxy A component is a repeating unit having an alkylene group bonded to oxygen.

The alkylene carbonate and alkylene oxy components are represented by the following formula, respectively: 1+C(R”)z C(R”)z OCO! ← and →C(Rst C(R”)z　to (In the above formula, R2 is defined below).

The acid functional polymer of the present invention is disclosed in U.S. Application No. 88 filed on July 14, 1986. 5.118 or by other known methods. (lukylene carbonate) polyal. This is a nonionic polymer with acidic group donors, such as cyclic anhydrides, acid anhydrides and halo acids in the case of -coon. This is done by reacting.

Preferred acid-functional polymers of the present invention include (1) (a) monofunctional alcohol, carbon Bonic acids, mercaptans, primary or secondary amines, C5-24 alkyl-substituted phenates nor or its C2~CSO alkoxylate and (b) alkylene carbonate Alkylene oxide and CO□, Alkylene carbonate, Alkylene oxide and and Cot mixture or addition with poly(alkylene carbonate) polyal Things (2) a substance that can react with this adduct to add an acidic end group; It is produced by reacting.

Many of the adducts formed prior to addition of the acid functional component are of known composition and have the following formula: %formula%) (In the above formula, R1 is 04~. Monofunctional alcohol, mercaptan, carboxylic acid, primary or secondary amine, or C3~, alkyl-substituted phenol or monofunctional functional alcohols, mercaptans, carboxylic acids, primary or secondary amines or It is a residue from 02-C1° alkoxylate of alkylphenol, and X is a unique Alkylene carbonate or alkylene oxide and CO are used Case - ZCOOC (R2) z C (R") z 0 - C (R2) 2 C (R2 )z-, and Z is 0. S, NH, or NR”, and R3 is C1,4 alkyl, and Y is independently alkylene carbonate or alkylene oxide or and when CO are independently hydrogen, ct-to alkyl, 07-2゜aralkyl, C6-4゜a Lyl, 07-2゜alkylaryl, C3-2゜alkenyl or inert position Exchange C3~. is a hydrocarbon, and l is described in co-pending U.S. application No. 885.118. Another initiator is added to the poly(alkylene carbonate) point as in the method described. is the residue of the initiator when used to form Rial, or 1985 1 U.S. Application Ni 1799.211 filed January 18 and December 16, 1985 Poly(alkylene carbonate) polya as per application k 809.675 When producing a roll, it is a residue of a modifier, and (■) preferably has a polyfunctionality of 04 to 0. alcohol, amine or mercaptan residue, n is independently 1 to 40; , m are independently O ~ 200, k is independently θ ~ 8, with the proviso that X, Y and I are randomly separated in the polymer main chain) It is expressed as

As mentioned above, the starting materials for the production of the acid functional polymers of the present invention are monofunctional alkaline Cole, mercaptan, carboxylic acid, primary or secondary amine, C844 alkyl Ruphenols or their alkoxylates and alkylene carbonates and/or ethylene oxide and CO2 and/or poly(alkylene carbonate). -bonate) polyal, as well as reacting with adducts to add a terminal acid component to the polymer. poly(alkylene carbonate) polyal formed from a donor that can Ru.

Effective monofunctional alcohols particularly suitable for the practice of this invention include C4-C1° alkyla alcohol and its C2-CSO alkoxylate derivatives, but other May be used. Alkoxylates are made by reacting alcohols with alkylene oxides. It is formed by Preferred monofunctional alcohols are 04-C24 alkylalk even more preferred monofunctional alcohol is C8-CtO alkyl alcohol, and the most preferred monofunctional alcohol is a C3-C11 alkyl alcohol. alcohols, such as octatool, dodecanol, tetradecanol, hexadeca alcohol and octadecanol.

Suitable monofunctional mercaptans for the preparation of the nonionic polymers of the invention are C4-C 3゜alkyl mercaptan and its C2~CSO alkoxylate derivative. However, others may be used. Alkoxylates convert mercaptans into alkylene oxides. Formed by reaction. Preferred monofunctional mercaptans are C4-CZ a alkyl mercaptan, more preferably C8-C2゜alkyl mercaptan most preferably a C3-C11 alkyl mercaptan, such as an octyl mercaptan. lumercaptan, dodecyl mercaptan and octadecyl mercaptan. . However, other mercaptans may also be used; The nonionic polymer composition is disclosed in the present inventor's U.S. application filed July 14, 1986. No. 885,118.

Monofunctional Cal for the Synthesis of Nonionic Poly(Alkylene Carbonate) Polyal As the boxylic acid, 04~C1゜alkyl carboxylic acid and its 02~C1゜alcoboxylic acid. Xylate derivatives may be used; alkoxylates are oxidized alkylates It is formed by reacting with Preferably c4-CZa alkyl carbo acid, more preferably 06-C2 alkylcarboxylic acid, most preferred or C6 to CI I alkyl carboxylic acids, such as lauric acid, stearic acid and and oleic acid. However, other carboxylic acids may also be used.

Suitable monofunctional primary amines for the synthesis of the nonionic polymers of the present invention are C4-C1 ゜alkylamines and their 02-C9゜alkoxylate derivatives. Like or 04-CH alkylamine, more preferably C8-C2゜alkyl amines, most preferably Cs-cps alkyl amines, e.g. amine, dodecylamine, tetradecylamine, hexadecylamine and octa It is decylamine. However, other primary amines may also be used. Alkoxylate is formed by reacting an amine with an alkylene oxide.

-04-C30 dialkylamines and alkoxy thereof as functional tertiary amino Sylate derivatives are preferred. Preferred tertiary amino is C4-C2'4 dialkyl amine, more preferably 06-CZO dialkylamine, most preferably or C8-CI8 dialkylamine, such as N,N-dioctylamine, N , N-didodecylamine, N-octyl-N-decylamine, N-methyl-N- Dodecylamine, N-methyl-N-octylamine, and N-methyl-N-o Railylamine, but others may also be used.

Suitable monofunctional alkylphenols include 03-C3° alkyl substituted phenols and It is a 02-C9° alkoxylate. More preferably C1-C24 alkyl Kyl-substituted phenols, even more preferably 03-C111 alkyl-substituted phenol, most preferably C4-C+ Z alkyl substituted phenol. Ru. However, other monofunctional phenols or their alkoxylates are also within the scope of this invention. Alkoxylates can be used in the reaction of altenol with alkylene oxide. It is formed by

The above monofunctional compounds include halo, cyano, nitrile, Other substituents such as nitroalkoxy, alkenes, thioalkyl, tertiary amino may be included.

In the above chemical structure, R1 is preferably halogen, lower alkyl, alkylene Monovalent hydrocarbons substituted with oxy and non-reactive substituents (including 0, N or S) It is an elementary group. R' more preferably contains one or more oxygen, nitrogen or sulfur components Aliphatic, alkyleneoxy, cycloaliphatic, aryl, alkylaryl or aliphatic It is a arylalkylhydrocarbyl residue. R1 is even more preferably hydrogen or or monohydric alkanes or alkylenes substituted with one or more oxygen, nitrogen or sulfur components. cycloalkanes or cycloalkanes. R' is even more preferably monovalent C4 ~C111 aliphatic or 06~C3° cycloaliphatic hydrocarbon.

R2 is preferably hydrogen, C3-C2° alkyl, CI-Cz.

Haloalkyl, C3-C2゜alkenyl or Ch''-Cz. phenyl more preferably hydrogen, C8-C, alkyl, C2-C, alkenyl or phenyl, even more preferably hydrogen, methyl or ethyl; Hydrogen or methyl is more preferred, and hydrogen is most preferred.

Each R2 is independently hydrogen, halogen, nitro, cyano, hydrogen or one or more halo, Ci-Cz substituted with acine, nitro, thioalkyl, tertiary amino. Hydroca Rubil, C, -% ICII alkoxy, 06-Cl8 aryloxy, 07-C 2゜Aralkoxy, carbonyldioxy (cr~C,s)alkyl, car Bonyldioxy(C&~C2゜)aryl, carbonyldioxy(Ct~C24 ) Aralkyl% CI% CII alkoxycarbonyl, C6-C1, ary oxycarbonyl, C? ~C2゜aralkoxycarbonyl, C1~CIl+ Alkylcarbonyl, C&-wc26 aralcarbonyl%C7~C2゜Ara alkylcarbonyl, C1-C83 alkylsulfinyl, C1-C2° Sulfinyl% C? ~C2゜aralkylsulfinyl, C1~C+　sal Kylsulfonyl, C6-C2゜arylsulfonyl or C1-C2゜ara May be rukylsulfonyl.

■ is the initiator used to produce poly(alkylene carbonate) polyal is the residue of ■ is typically a polyfunctional alcohol, mercaptan or amino acid. It is a residue from a polyal as shown in the figure. Polyfunctional alcohols are polyols, e.g. Glycerin, ethylene glycol, 1,4-butanediol, polyether polyester polyols, polyester polyols, and hydroxy-functional acrylic acid polymers -Including. Polyfunctional mercaptans include 1,6-hexanedithiol, 1,12- Polyfunctional compounds including dodecanedithiol and 1,18-octadecanedithiol Valid amines include 1,6-diamithexane and 1,12-diaminododecane However, other initiators may also be used within the scope of the invention.

monofunctional alcohol, carboxylic acid or primary or tertiary amino, or alkyl phenol or its alkoxylate and alkylene carbonate or Nonionic poly(alkylene carbonate) obtained from alkylene oxide and CO□ The polyal may be formed by any method known in the art.

Alcohol initiated reactions of alkylene oxide and CO2 are operated within the scope of this invention.

In addition, the nonionic polymer is filed by the same inventor on July 1, 1985, published in the United States @Nα 750.362; 885.118; 198 filed on July 14, 1986 Nα799.211 filed on November 18, 1985; and December 16, 1985 Produced by the method described in application No. No. 809,675.

The ratio of X to Y in the poly(alkylene carbonate) polyal is used The method and molar ratio of reactants, as well as the temperature, time, catalyst and catalyst concentration of the reaction Determined by conditions. The nonionic poly(alkylene carbon) thus formed polyal is a random polymer, and the ratio of X, Y and The length of the mer is determined by the values of n, m and k. The values of n, m and k are additive Used to change the average molecular weight of a substance.

The preferred value of n is 1 to 40, more preferably 1 to 20, and most preferably A preferred value of 0m is 1 to 10, more preferably 0 to 200, and more preferably 0 to 200. 100, and even more preferably 0 to 50. Preferably the value is O~8. Yes, more preferably 0-3, even more preferably 0-1.

The preferred average molecular weight of the polymer is 300 to 10.000, more preferably It is 300-5000, and even more preferably 500-3000.

Preferred acid terminal components are -COOH, 5OzH, 5O3H, 5oak.

POJt, or -POJz, or sulfosuccinate.

The novel acid functional poly(alkylene carbonate) polyal of the present invention is produced by the following formula: expressed.

R1-(X), -(Y), -(1)k-0-A (in the above formula, R', X, Y, I, (n, m and k are as defined above and A is an acid functional component) In embodiments, A is represented by the following formula.

-(R'), -B (In the above formula, R4 is alkylene, carbonylalkylene, alkenylene, carbonyl alkenylene, (C1~es)arylene, or cycloalkenylene, B is an acid terminal component) Can react with poly(alkylene carbonate) polyal to add terminal acidic groups. Examples of acid donors selected from a large number of compounds known in the art include the following: The following is provided.

Alkyl cyclic anhydride, cycloalkyl cyclic anhydride, aryl cyclic anhydride, alkyl cyclic anhydride, A ring selected from the group consisting of ruaryl cyclic anhydride and aralkyl cyclic anhydride. Formula anhydrides, among these, more preferred are 04-Cza alkyl cyclic anhydrides , 08-C24 cycloalkyl cyclic anhydride, C8-C14 aralkyl cyclic anhydride and C8-Cta alkylaryl monocyclic anhydride. This anhydride is halogen may be substituted with carbonyl, alkyl, alkylcarbonyl and aryl. There is no example Hydrosuccinic anhydride, maleic anhydride, phthalic anhydride, bromomaleic anhydride, dichloroanhydride Romaleic acid, dimethylmaleic anhydride, dimethylsuccinic anhydride, 2-dodeceanhydride -1-yl succinic acid, glutaric anhydride, hebutanoic anhydride, hexanoic anhydride, anhydride Homophthalic anhydride, 3-methylglutaric anhydride, methylsuccinic anhydride, and 2-methyl anhydride The most preferred anhydrides include phenylglutaric acid, succinic anhydride, and maleic anhydride. , and phthalic anhydride.

However, monofunctional alcohols, mercaptans, carboxylic acids or Any anhydride that can react with a triamine to give a 7-terminal carboxylic acid component. May be used.

The formation of sulfosuccinates is a special case of cyclic anhydride reactions. poly(a) (lukylene carbonate) polyal with maleic anhydride and sodium bisulfite react with mu. The sulposuccinate component has the following formula.

Other types of compounds that can add terminal acid groups to nonionic polymers are Compounds containing sulfonic acid, sulfinic acid or sulfuric acid terminal components and their salts. Examples include /% rosulfonic acid and its salts, such as chlorosulfonic acid, chlorosulfonic acid and its salts. Sodium rosulfonate and chloroethylsulfonic acid may be used; Among these, preferred are chlorosulfonic acid, chlorosulfinic acid and chloroethyl It is sulfinic acid.

Since acidic groups are added to the polymer to form the acid-functional polymer of the present invention, Yet another group of compounds that can be used are halocarboxylic acids and their salts, such as chloroacetic acid, Sodium loroacetate, bromoacetic acid, and chloropropionic acid. most preferred The most suitable one is monochloroacetic acid. Still others capable of adding terminal acidic groups The group of compounds is inorganic acid anhydrides such as P, 0° and SOs.

Typically, non-ionic poly(alkylene carbonate) polyamides are produced without decomposing the adduct. Any compound capable of adding a terminal acidic group to a polymer is suitable for use in the present invention. suitable for

Addition of acidic end groups to poly(alkylene carbonate) polyal uses acid depending on the quality and the nature of the monofunctional substance.

Cyclic carboxylic acid anhydrides are the most preferred materials used to add terminal acid groups. It's a nice kind.

The reaction is carried out at a temperature of 80°C to 180″C for a few minutes to several hours. carbonate) by contacting a polyal with a cyclic carboxylic acid anhydride. Ru. Optionally, a basic catalyst, such as an alkali metal or alkaline earth metal carbonates, alkoxides, stannate or borates, or Tertiary amines may be used. Preferably, no catalyst is used, thereby removing the catalyst after the reaction. Eliminating the need for removal.

Active hydrogen groups on poly(alkylene carbonate) for cyclic carboxylic acid anhydrides The molar ratio of is 1:1 or more, but the acid component contained per molecule is No more than 1.

Chemically attaching carboxylic acid functional components to the ends of poly(alkylene carbonate) polyal The reaction is preferably carried out in the absence of a solvent and the product is May be used in many applications without further purification, but this reaction may be It may be carried out in the presence of an inert solvent. Conversion of cyclic carboxylic acid anhydrides is most often That's 100%.

When using a haloacid as a source of acid component, such as pyridine or triethylamine, In the presence of a compound capable of acting as an acid acceptor, poly(( alkylene carbonate) may be added to the polyal. The product thus obtained , neutralization, removal of by-product salts and removal of solvent.

Salts of novel acid-functional polymers, such as alkali metal salts, alkaline earth metal salts, alkali metal salts, Kylammonium, cycloalkylammonium, alkylaryl ammonium amine salts, such as aryl ammonium and aralkyl ammonium salts; Various known neutralizing substances may be used to obtain ammonium salts.

The choice of the particular neutralizing agent used will depend on how different salts interact with other materials in the end use. Depending on the particular salt needed for a particular application, it will have different compatibility. different. Ammonia, methylamine, dimethylamine, trimethylamine, ethylamine amines, propylene amines, butyl amines and long chain alkyl amines (Cm.

Amines are one preferred type, such as alkylamines (up to alkylamines). But this Others may also be used. Among alkali metal salts, lithium, sodium and and potassium are most preferred. Among alkaline earth metal salts, calcium and Gnesium is most preferred.

The method of neutralizing acid-functional poly(alkylene carbonate) polyal is important. Ru. When strong chlorine is used, such as with alkali metal hydroxide, the amount of neutralization There must never be a residue, since such a condition is This is because it causes hydrolysis of the polyal main chain (bonate).

Amines, such as ammonia, are particularly effective because local excess does not cause backbone hydrolysis. It is. Typically, acid-functional poly(alkylene carbonate) is added while monitoring the pH of the product. - Bonnet I-') Slowly add the neutralizing agent to the polyal. In this method, acid The desired percentage of components is neutralized up to 100 percent.

Novel acid-functional poly(alkylene carbonate) polyal polymer containing its salt The characteristics of the nonionic poly(alkylene carbonate) for acid group donor compounds are g) Improved by adjusting the ratio of polyal. Io to non-ionic It is desirable that the ratio of properties varies depending on the specific application for which the polymer is used; therefore, If a polymer product with highly anionic properties is desired, a non-ionic The ratio of flexible polymers is 1:1. This is a non-ionic bond to an anionic polymer. Provides a complete transformation of Rimmer.

However, other applications require a different balance of nonionic and anionic surfactant capacity. It is essential. In such cases, partial conversion of the nonionic polymer to acid functionality is Desirably, it eliminates non-ionic and acid functional components (such as those present in the product). do. The ratio of nonionic polymer to acid group donor is particularly important for only small amounts of anion. If you want on characteristics, set it as high as possible.

A 20:1 ratio of nonionic polymer to acid groups is within the scope of this invention. acid group A particularly useful range of the ratio of nonionic polymer to More preferably, it is 1.5:1-181.

The characteristics of the new acid-functional bone polymer and its salts include, for example, the main polymer, the Polymer carbonate and/or alkylene carbonate: ratio of monofunctional compounds in the polymer backbone, polymer molecular weight, acid functional groups present as salts and the composition of the cationic and ionic portions of the salt.

In some cases, nonionic polymers different from the acid-functional polymers of the invention A mixture with is a more suitable solution. Additionally, for other purposes, the anions of the present invention After the ionizing surfactant is prepared, additional nonionic surfactant is physically mixed. this The nonionic poly(alkylene carbonate) used as the starting material is useful for the application. -carbonate) polyal or other known poly(alkylene carbonate) polyal It is Earl. Also, US application filed on December 16, 1985 @ No. 809,6 75 or the modified polyester described in k 799.211 filed on November 18, 1985 Other nonionic polymers such as (alkylene carbonate) polyals are also suitable. be. Other nonionic polymers can be added to the ionic surfactants of the invention, such as polyethers. Terpolyals, polyester polyals, alcohol ethoxylates and fluorescein May be used in combination with phenol ethoxylates.

The surfactants of the present invention may be used in combination with other anionic surfactants. Examples of anionic surfactants such as carboxylic acids, oxyacetates, sulfones -, ether sulfates, phosphates, sulfosuccinates and the like Contains salts from

The anionic surfactant of the present invention has a corresponding nonionic surfactant for various applications. It is used in much smaller amounts than the drug. anionic field to reduce the surface tension of water When using a surfactant, only 10 times the amount of nonionic surfactant required Only volume percentages are required.

When used alone, it is effective in amounts of 0.0002 to 10 weight percent. Ru. Preferably 0.0005 to 2 weight percent of the total volume, more preferably 0.0005 to 2 weight percent of the total volume. 001 to 1 weight percent.

When used in combination with other surfactants, the new polyal has a final volume of 0.0 002-5 weight percent, more preferably 0.0005-2 weight percent, Even more preferably it is incorporated in an amount of o,ooi to 1 weight percent. but , the amount of surfactant incorporated into such compositions may vary depending on the appropriate or It may be outside the above necessary range.

The amount of other surfactants incorporated into the composition may vary depending on the particular application. other Such amounts of surfactants are usually about the same as those mentioned above.

Having generally described the invention, the following examples are illustrative and limit the scope of the invention. Unless otherwise indicated, all parts and percentages are by weight. .

, 1: Reaction product of ethylene carbonate (EC) and alcohol Known methods such as U.S. Pat. No. 4.330.48 to Timber 1ake These were manufactured according to No. 1. Desired molar ratios of EC and alcohol (see Table 1) ) in the presence of sodium stannate trihydrate (1% by weight) as a catalyst in a nitrogen atmosphere. The mixture was heated while stirring.

After the reaction was completed, fluorosil (1 g/101 g raw) was added for 3 hours. product) (20 weight percent in acetone), followed by filtration or The catalyst was removed by solvent removal. The characteristics of the product are shown in Table 1.

Table 1 = Reaction product of ethylene carbonate and alcohol＼n-butano-y& 10 25 160 99.6n-hexanol 10 25.5 150 98.0-n-Octano-31022160100,ODn-Deca/- 1102216099, 4E n -Ff *) 4 5 21.5 160 10 0. OFn -F Decane-+L 10 21.5 160 100. OG　n　 -F Decano is 20 21.5 160 96.512: E C: n- Reaction product of octatool (No: 1) adduct and succinic anhydride 50 units equipped with a stirrer, cooler, thermometer and temperature controller and kept under nitrogen atmosphere Ethylene carbonate (331.95 g, 3.768 mol) was placed in a M flask. ) and n-octatool (49,07 g, 0.3768 moa tz) Ta. The reactor was heated to 175°C and sodium stannate trihydrate (3.81 g, 1. 0 weight percent) was added as catalyst. Stop the reaction after 7 hours at 175°C. It stopped.

The EC conversion rate was 97.5%.

Part of the above EC: n-octatool product (226.1 g, 0.30 mol oxy) and succinic anhydride (30.0 g, 0.30 mol) in the same reaction vessel as above. and heated at 120°C for 1 hour. Proton NMR and capillary gas Chromatographic analysis both showed 100 percent conversion of succinic anhydride. Ta. A solution of the product (20 weight percent) in acetone was prepared with Fluorosil. (Ig/10g product), stir for 3 hours, filter, and remove the solvent on a rotary evaporator. The catalyst was removed by evaporation. The adduct was a straw-colored viscous liquid.

The results of NMR analysis were as follows.

0.7-1.8 6 (Multiplet, CH3 (CHI) 4-51.00) 2.9-3 ．． 1 6 (-doublet, -0zCCHtCHzCCh-10,94) 3.4 to 4.0 5 (multiplet, -CHzOCHz-,6,39) 4.1 to 4.5 6 (multiplet, -C)lzOCOzCHz-54,23) IR data were consistent with the structure shown.

M, , = 552, T, = 1,101, P D I = 1.99 Titration: 1 ．． A part of the 105 meq COJ/g adduct was converted to 2-hydro as follows. Converted to xyethylamine salt. Adduct (2,50 g) and 100 mfl desorption Ionized water was placed in a 4 oz (113 g) bottle and shaken. Insoluble sticky white solid I got a body. 2-Hydroxyethylamine was then added while monitoring the pH. p When H reaches 6620, drain the contents of the bottle into a 250-volume volumetric flask with deionized water. This salt was quite water soluble (2.50 g nonionic surfactant). /250g = 1.00 weight percent anionic surfactant).

Surface tension was investigated as a function of concentration. The results obtained are shown in Table 2.

Table 2: Surface tension (dyne/Ω) 1,0 31.2 Insoluble 0.4 32.2 Insoluble 0, 1 35.3 32.2 0.04 35.4 37.3 0.01 39.9 44.3 0.004 39.2 60.0 0.002 39.0 61.7 This result shows that the anionic surfactants of the present invention compared to non-succinic anhydride-capped congeners. It has 10 times more water solubility when This indicates that it has surface activity.

■Main: EC: reaction product of n-dodecanol (10:1) adduct and succinic anhydride Ethylene carbonate (310.50 g, 3.524 mol), n-dodecano (65,67 g, 0.352 mol) and sodium stannate trihydrate (3,7 6 g, 1.0 weight percent) were mixed in the same reaction system as Example 2. The reaction vessel was heated at 175°C for 6 hours. The EC conversion rate was 95.7%. Ta.

Part of the above EC: n-dodecanol product (243.0 g, 0.30 mol Roxy) and succinic anhydride (930.0 g, 0.30 mol) in the same reaction as in Example 2. placed in the apparatus and heated at 120″C for 1 hour. Proton NMR and capillary Gas chromatography analysis showed 100 percent conversion of succinic anhydride in both cases. did. The catalyst was removed as in Example 2. The adduct was a straw-colored viscous liquid. .

The results of NMR analysis were as follows: 0.7-1°9 δ (multiplet, CH z (CH2) b-11,00) 2.6 to 2.8 δ (-multiplet, -0zCCH zC) IzC (h-10,99) 3.5-460 δ (multiplet, -CH20CH 2-, 5゜81) 4.1 to 4.5 6 (multiplet, -CH20CO□CRZ-14 , 18) IR data were consistent with the structure shown.

T,, = 6i1, T, = 1,044, P D I = 1.71 Titration: 1.103meq COJ/g ■Soil:EC:n-butanol (10:1) addition Reaction product between succinic anhydride and succinic anhydride ethylene carbonate) (180.87g, 2.053mol), n-butanol (15,22 g, 0.2053 mol) and sodium stannate trihydrate (1,9 6 g, 1.0 weight percent) as in Example 2 except using a 250-flame. The mixture was mixed in the same reactor and the reaction vessel was then heated to 150°C for 20.5 hours. . The EC conversion rate was 95.0%.

Part of the above EC: n-butanol product (144.0 g, 0.2O-f-ruhi (Droxy) and succinic anhydride (20.0 g, 0.20 mol) in the same reaction as in Example 2. The mixture was placed in an apparatus and heated at 120°C for 1 hour. Proton NMR and capillary gas Chromatographic analysis both showed 100 percent conversion of succinic anhydride. Ta. The catalyst was removed as in Example 1. The adduct was a straw-colored viscous liquid.

The results of NMR analysis were as follows: 0.7-1.96 (multi-ring, C1 h (CHt) b-11,00) 2.6 to 2.8 6 (- doublet, -〇□CCH zC)IzCO□-11,06) 3.5-4.0 δ (multiple ring, -C)lzOC Hz-, 6, 27) 4.1-4.5 6 (multi-ring, -C) 1. OCO□CHz- (15,64) IR data were consistent with the structure shown.

H, = 589, Side- = 1.030, P D I = 1.75 Titration: 1. 159meq C (hH/g [5: E C: n-octatool (10:1 ) Reaction product between adduct and maleic anhydride Ethylene carbonate (175.54g, 1.993mol), n-octatwo (25,95 g, 0.1993 mol) and sodium stannate trihydrate (2, 02g, 1.0% by weight) were mixed in the same reaction system as Example 4. The reaction vessel was heated at 150°C for 16 hours. EC conversion rate is 87.0% Met.

Part of the above EC: n-octatool product (155.2 g, 0.19 mol oxy) and maleic anhydride (18.63 g, 0.19 mol) as above. The mixture was placed in a reactor and heated at 120°C for 1 hour. Proton NMR and capillary Rigas chromatography analysis shows 100% maleic anhydride in both cases. It showed a transformation.

The catalyst was removed as in Example 2. The adduct was a straw-colored viscous liquid.

The results of NMR analysis were as follows: 0.7-1.86 (multi-ring, CH s (CHz) b-11,00) 3.5-3.9 6 (multiple ring, -CHzOC Hz-, 5, 23) 4.1 to 4.5 6 (multi-ring, -CHzOCOzCHz-1 4,77) 6.2-6.3 6(-doublet, -〇□CCtl=CHCO□-10, (91) IR data were consistent with the structure shown.

Titration: 1.028meq C0zH/g18Ec nioleyl alcohol (1 0:1) Reaction product of adduct and succinic anhydride Ethylene carbonate (153,76g, 1.745mol), oleylalco (46.77 g, 0.1745 mol) and sodium stannate trihydrate (2 00g, 1.0 weight percent) were mixed in the same reactor as Example 4. Then anti The reaction vessel was heated at 150''C for 23 hours.

The EC conversion was 95.1 percent.

A portion of the above EC nioleyl alcohol product (158.0 g).

0o17 mole hydroxy) and succinic anhydride (17.0 g, 0.170 mole, l ) was placed in the same reactor as above and heated at 120°C for 1 hour.

Pro-1-NMR and capillary gas chromatography analyzes are both free. It showed 100 percent conversion of hydroxysuccinic acid.

The catalyst was removed as in Example 2. The adduct was a straw-colored viscous liquid.

The results of NMR analysis were as follows: 0.7-1.96 (multi-ring, olefin) il, 1.00) 2.6~2゜7　δ(-multiplet, -0zCC)IzCHzCOz -10,68) 3.5-3.9 δ (multi-ring, -CH2OC) 12-. 3.18 )4.1~4゜5　δ(Multiple ring, -CH,OCO□cnz-12,94) IR data The data were consistent with the structure shown.

π, = 618, T, = 906, P D I = 1.47 Titration: 0.7 62meq cozH/g [7: E C: with n-dodecanol (5:1) Reaction product of additive and succinic anhydride A portion of Sample E from Example 1 (35,000 g, 0.1027 mole hydroxy), no Hydrosuccinic acid (10.27 g, 0.1027 mol) and sodium stannate trihydrate (0.45g, 1.0% by weight) was heated at 120°C for 1 hour. proto NMR showed complete conversion of succinic anhydride.

The catalyst was removed as in Example 2. The adduct was a straw-colored, low viscosity liquid.

The results of NMR analysis were as follows: 0.7-1.96 (multi-ring, CH s (CHz) &-11,00) 2.6 to 2.7 5 (-multiplet, -〇□CCH zCIhC (h-11,02) 3.6-3.9 6 (multi-ring, -CHzOCHt -,2,6)4.1-4.5　6(multi-ring, -cnzOcO□CRZ-12,2 ) T, = 405, ■, = 500, P D I = 1.23 Titration: 2.5 40meq C0zH/g■ Main: EC: With n-dodecanol (2081) Reaction product of additive and succinic anhydride A portion of Sample G of Example 1 (26.19 g, 0.0353 mole hydroxy), no Hydrosuccinic acid (3,53 g, 0.0353 mol) and sodium stannate trihydrate (0.29g, 1.0% by weight) was heated at 120°C for 1 hour. proton NMR spectrum showed complete conversion of succinic anhydride. The catalyst was removed as in Example 2. I left. The adduct was a straw-colored viscous liquid.

The results of NMR analysis were as follows: 0°7-1.96 (multi-ring, CH 3 (cHz) 6-11゜00) 2.6-2.7 6 (-multiplet, -〇□CCHz CHzCO2-11,21>3.6-3.9　6 (multi-ring, -CHzOC)lz -,10,6)4゜1~4.5　6(multiple ring, -CHzOCOzCHz-18, 7) M, = 868, M, = 1.730, P D 1 = 1.99 Titration: 1.221meq C0zH/gl:Ec:With n-butanol (25:1) Reaction product of additive and succinic anhydride Ethylene carbonate (213.63g, 2.425mol), n-butanol (7,19 g, 0.0970 mol) and sodium stannate trihydrate (2-20 g, 1.0 weight percent) were mixed in the reaction system used in Example 4. This anti The reaction vessel was heated at 150°C for 49 hours, resulting in an EC conversion of 90.0 percent, 24 Weight percent CO2 was obtained. Succinic anhydride (9.70g, 0.097mol) ) was added and the reaction mixture was heated at 120°C for 1 hour. Proton NMR minute Analysis showed complete conversion of succinic anhydride. The catalyst was removed as in Example 2. addition The substance was a straw-colored liquid.

The results of NMR analysis were as follows.

0.7-1.9 δ (multiple ring, CH3 (CHz) z-11,0) 2.6-2. 7　6(-multiplet, -〇□CCHzCHzCOz-21゜0)4゜1~4.5　5 (Multiple ring, -CHzOCOzCHz-115,2)T, =755, M, =2,274, PDI =3.01 Titration: 0.493meq C0z H/g [1i1: E C: n-octatool (10:1) adduct and anhydride Reaction products with phthalic acid Ethylene carbonate (174.78g, 1.984mol), n-octatwo (25,84 g, 0.1984 mol) and sodium stannate trihydrate (2, 00 g, 1.0 weight percent) were mixed in the same equipment as Example 4. This reaction vessel was heated at 150° C. for 16 hours, resulting in an EC conversion of 94.5 percent. anhydrous Phthalic acid (29.33 g, 0.198 mol) was added and the reactants were heated at 120° C. for 5 hours. It was heated for a while. The catalyst was then removed as in Example 2. The adduct is a straw-colored viscous It was liquid.

The results of NMR analysis were as follows.

0.7-1.9 6 (multiplet, CH3(CH2) b-11,0) 3.5-4. 0 6 (multiplet, -CHzOCHz-,5,73) 4.1 to 4.5 6 (multiplet , -CH20CO□C1h-24,55) 7.5-8.0 6 (multiplet, aromatic , 0.99) T, = 879, π u = 1.025, P DI = 1.92 Titration: 1.021 meq coin, / g Selected characteristic data corresponding to the above example The data and surfactant properties are shown in Table 3.

Top row: poly(ethylene carbonate) polyol and n-octadecyl mercap Reaction products with tan and succinic anhydride Poly(ethylene carbonate) polyol (πゎ2076.27.4 weight percent ethylene oxide and diethylene glycol using diethylene glycol as an initiator. Produced from carbon dioxide and carbon dioxide.

Poly(ethylene carbonate) polyol sample (100,1 g), n- Octadecyl mercaptan (17,19 g) and sodium stannate trihydrate ( 0.59 g) were mixed in the same equipment used in Example 4. Boil the flask at 175°C for 5 hours. It was heated for a while. On cooling to ambient temperature, the product (113,5 g) becomes a white wax (M, 1457).

A portion of white wax (81.3 g, 0.0792 mol) and succinic anhydride (7 , 92g, 0.0792mol) was placed in the same apparatus as above and heated at 120°C for 1 hour. It was hot. Size exclusion chromatography shows 100 percent succinic anhydride conversion. did. Proton NMR was consistent with the structure shown. Zero surface tension was 46.5 dynes/c. m (0.1 percent aqueous solution of ammonium salt: 23°C).

This example demonstrates that mercaptans may be used to prepare the novel compositions of the present invention. It shows.

■u: Poly(ethylene carbonate) polyol and n-dodecylamine and nothing Reaction product with hydroxysuccinic acid The same poly(ethylene carbonate) poly used in Example 11 A sample of ol (100,2 g) and n-dodecylamine (27,80 g ) Heated for an hour. Upon cooling to ambient temperature, the product (122,9 g) turns into a white wax. (Vka 1019).

A portion of white wax (89.3 g, 0.185 mol) and succinic anhydride (18 , 4g, 00185 mol) was placed in the same apparatus as above and heated at 120°C for 1 hour. . Size exclusion chromatography showed 100 percent succinic anhydride conversion.

NMR spectrum data are as follows.

0.7-1.6 6 (multiplet, CI (+ (CHHz) r.-11°0) 2.6 -2.8 6 (-multiplet, -〇□CCHzCH2CO□-11,2) 3.4~3. 9　δ(multiplet, -CHzOCHz-,9,6)4゜0~4゜5　δ(multiplet, -CHzOCOzCL-13,8) The surface tension is 34.4 dynes/cm (ammonium 23° C.).

This example shows that amines may be used to prepare the novel compositions of the present invention. There is.

1: Poly(ethylene carbonate) polyol and n-hexadecylamine and reaction product with succinic anhydride and the same poly(ethylene carbonate) used in Example 11. A sample of polyol (100.3 g) and n-hexadecylamine (27 , 80 g) were mixed in the same equipment used in Example 4. The flask was heated to 125℃ for 6 hours. Heated. Upon cooling to ambient temperature, the product (114.4 g) was a white wax. There was (π, 1657).

A portion of white wax (82.0 g, 0.1335 mol) and succinic anhydride (1 3.35g, 0.1335mol) was placed in the same equipment as above and heated at 120℃ for 1 hour. It was hot. Size exclusion chromatography showed 100% succinic anhydride conversion. did. Proton NMR was consistent with the structure shown.0 surface tension was 40.5 dynes/C. I (0.1 percent aqueous solution of ammonium salt; 23° C.).

■■: Ethylene carbonate: n-hexanol (10:1) adduct and anhydrous 2- Reaction product with dodecen-1-yl succinic acid Ethylene carbonate (357.3g, 4.056mol), n-hexanol (41,44 g, 0.4056 mol) and sodium stannate trihydrate (3,9 9 g, 1.0 weight percent) were mixed in the reaction system used in Example 2. frass was heated at 160°C for 25.5 hours, and the ethylene carbonate conversion rate was 98.0%. It was cents.

A portion of the product formed above (70,0g, 0.0957 mol OH) and no Water 2-dodecen-1-ylsuccinic acid (28.42 g, Q, 0957 mol) Example 1 The mixture was placed in the same apparatus used in 1 and heated at 120°C for 2 hours.

Proton NMR spectral data were consistent with the structure shown.

Surface tension is 35.7 dynes/mark (0.1 percent aqueous solution of ammonium salt; 2 3°C).

This example demonstrates that substituted succinic anhydrides may be used to prepare the novel compositions of the present invention. It shows.

■Dan: Use of the surfactant of the present invention to produce water-based polyols A, Modified poly(ethylene carbonate) polyol (70.9%, P -725 modified, M, 1937.5.0 g) and water (5,0 g) for stirring. More mixed. The mixture immediately separated into two immiscible liquid phases. Water (1, A solution containing the surfactant of Example 3 (0.5 g) as an ammonium salt dissolved in The liquid was added with stirring. A white emulsion forms and slowly dissolves when left overnight at ambient temperature. easily separated and redispersed.

Using the surfactant of Example 6 (as ammonium salt) instead of the surfactant of Example 3 The same experiment as above was repeated with the following exceptions. A white emulsion formed. Ambient temperature After standing overnight, only a portion of the resin separated, which was easily redispersed.

B, modified poly(ethylene carbonate) polyol (51.2%, P -725 modified, M, 12141.3.0 g) and water (3.0 g) for stirring. More mixed. The mixture separated into immiscible liquid phases as soon as stirring was stopped.

Surfactant of Example 3 (0.3 g) as ammonium salt dissolved in water (0.7 g) was added with stirring. A white emulsion forms and stands overnight at ambient temperature. It separated slowly and was easily redispersed.

C0 modified poly(ethylene carbonate) polyol (27,7 percent, P- 425 modified, Mn2132.11.2g) and water (9.5g) were mixed by stirring. It matched. The mixture immediately separated into two immiscible liquid phases. water (1.5g) A solution containing the surfactant of Example 3 (0.56 g) as an ammonium salt dissolved in Added with stirring. A white emulsion forms, which is 300 cps (0,3 Pa- s) had a Brookfield viscosity of (modification before conversion to water-based liquid) Brookfield viscosity of poly(ethylene carbonate) polyol is 14.9 00 eps (14,9 Pa-5)). This emulsion was allowed to stand overnight at ambient temperature. Then, it separated but was easily redispersed.

D, 2000 molecular weight poly(propylene glycol) (10,0 g) and water (10.0 g) were mixed by stirring. This mixture immediately forms two immiscible liquids Separated into phases. Surfactant of Example 3 as ammonium salt dissolved in water (2,0g) A solution containing the agent (1.0 g) was added with stirring. A white emulsion forms, which is It was stable after standing overnight at ambient temperature.

E, 2000 molecular weight diethylene glycol adipate diol (For+w rez 11-56+ made by Witco Chemical Company, 3 ．． 3 g) and water (3.3 g) were mixed by stirring. This mixture consists of two immiscible separated into a compatible aqueous phase. Example 3 as ammonium salt dissolved in water (0.7 g) A solution containing surfactant (0.30 g) was added with stirring. A white emulsion forms However, this separated after standing overnight at ambient temperature and was easily redispersed.

This example shows that the novel surfactant of the present invention is polyether polyol, polyester polyol, Water-based systems of all and modified poly(alkylene carbonate) polyals It has been shown that this method is effective in the production of products.

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Claims (10)

[Claims] 1. Poly(alkylene carbonate) backbone and average of at least 0.0% per molecule. An acid functional polymer having a terminal acid group of 05 or more and 1 or less, or a salt thereof. 2. (1) Monofunctional C4-30 alcohol, alcohol alkoxylate, merca Butane/mercaptan alkoxylate, carboxylic acid, carboxylic acid alkoxylate primary or secondary amines, primary or secondary amine alkoxylates, C 3-24 alkylphenol or alkylphenol alkoxylate (a) alkylene carbonate, (b) alkylene oxide and carbon dioxide, (c) alkylene carbonate, oxidation alkylene and carbon dioxide or (d) Obtained by reacting with poly(alkylene carbonate) polyal random poly(alkylene carbonate) polyal and (II) a residue of the donor capable of reacting with said reaction product to add a terminal acidic group; The acid-functional polymer according to claim 1, comprising: 3. A donor capable of reacting with the reaction product to add a terminal acidic group is a cyclic organic Acid anhydrides, halo and haloalkyl sulfonic acids, halo and haloalkyl carboxylic acids 3. The polymer according to claim 2, wherein the polymer is selected from the group consisting of phosphoric acids and inorganic acid anhydrides. 4. A donor capable of reacting with the reaction product to add a terminal acidic group is added to anhydrous amber. acid, cyclic organic acid anhydride selected from the group consisting of phthalic anhydride and maleic anhydride 4. The polymer according to claim 3, which is a polymer. 5. The acid-functional polymer according to claim 1 in the form of a metal salt, amine salt or ammonium salt. Rimmer. 6. The formula below, R1-(X)n-(Y)m-(1)k-O-A (in the above formula, R1 is independently C1-2 4 aliphatic, C6-24 cycloaliphatic, C containing 1-30 alkyleneoxy components 1-24 aliphatic or C6-24 cycloaliphatic alkoxylate, C3-24 aliphatic alkyl-substituted phenol or one or more substituents containing oxygen, nitrogen or sulfur C3-24 alkyl substituted with -ZCOOC(R2)2-C (R2)2-O-C(R2)2-C(R2)2-, where Z is independently -O , -S, -NH, or -NR3, and R3 is C1-24 alkyl. and Y is independently -OC(R2)2-C(R2)2-, where R 2 is independently hydrogen, C1-20 alkyl, C1-20 haloalkyl, C1-20 a rukenyl or phenyl, 1 is independently a polyfunctional C2-24 aliphatic, C6-30 cycloaliphatic, or C6-3 0 aromatic alcohol, mercaptan, amine or phenol (optional with oxygen) , may contain one or more types of nitrogen or sulfur), m is independently 0 to 200, n is independently 1 to 40; k is independently 0 to 8; A is an acid functional component, where X, Y and I are randomly arranged in the polymer backbone. It is location) The acid functional polymer according to claim 1, which has the following. 7. R1 is independently a monovalent C1-20 alkane, or 1-15 alkylene oxy contains hydrogen or one or more oxygen, nitrogen or sulfur components. C6-20 cycloalkane or C6-20 alkyl, R2 is independently hydrogen, halogen, nitro, cyano, hydrogen or one or more halo, cyano, C1-20 hydrocarbyl substituted with ano, nitro, thioalkyl, tertiary amino , C1-C18 alkoxy, C6-C18 aryloxy, C7-C20 arua alkoxy, carbonyldioxy (C1-C18) alkyl, carbonyldioxy (C6-C20) aryl, carbonyldioxy (C7-C20) aralkyl , C1-C18 alkoxycarbonyl, C6-C20 aryloxycarbonyl , C7-C20 aralkoxycarbonyl, C1-C18 alkylcarbonyl, C6-C20 aralkylcarbonyl, C7-C20 aralkylcarbonyl, C1 ~C18 alkylsulfinyl, C6-C20 arylsulfinyl, C7-C 20 aralkylsulfinyl, C1-C18 alkylsulfonyl, C6-C2 0 arylsulfonyl or C7-C20 aralkylsulfonyl, and A is represented by the formula -(R4)9-B, where R4 is carbonylalkylene, carbonyl Nylalkenylene, C5-8 arylene, alkylene, alkenylene or silyl is chloroalkylene, and B is -COOH, -SO2H, -SO3H, -SO4H , -PO4H2, PO3H2 or a residue of sulfosuccinate. Acid-functional polymers as described. 8. Monofunctional (C4-C30) alcohols, carboxylic acids, primary or secondary amino acids mercaptan, (C3-C24) alkylphenol or its alkoxy rate (a) alkylene carbonate (b) Alkylene oxide and CO2 (c) alkylene oxide, alkylene carbonate and CO2, or (d) Random nonionic reaction with poly(alkylene carbonate) polyal (alkylene carbonate) polyal obtained, Mixing a compound that can react with the reaction product to add a terminal acidic group (the above compound The random nonionic poly(alkylene carbonate) polyal ratio is 20:1-11) Acid-functional poly(alkylene carbonate) produced by a method comprising ) Poliar. 9. 5 to 95 weight percent of the acid functional polymer according to any one of claims 1 to 7. and a nonionic polymer (this nonionic polymer is a nonionic poly(alcohol) Kylene carbonate) polyal, polyether polyal, polyester poly R, alcohol alkoxylate, alkylphenol alkoxylate, selected from the group consisting of carboxylic acid alkoxylates and amine alkoxylates A surfactant composition comprising 95 to 5 weight percent of 10. The surfactant composition according to claim 9, and polyether polyal, polyal Consists of ester polyal and poly(alkylene carbonate) polyal A stable water-based emulsion or dispersion comprising one or more substances selected from the group consisting of: