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Publication numberUS3652583 A
Publication typeGrant
Publication dateMar 28, 1972
Filing dateMar 11, 1969
Priority dateMar 14, 1968
Publication numberUS 3652583 A, US 3652583A, US-A-3652583, US3652583 A, US3652583A
InventorsHiroshi Fukuhara, Katsumi Kobayashi, Shigeru Tajima, Shigeru Ura, Hiroki Yamamoto
Original AssigneeSumitomo Chemical Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Condensates of imidazolidone derivatives and polyalkylene glycol useful for improving textile materials
US 3652583 A
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Description  (OCR text may contain errors)

United States Patent 3,652,583 CONDENSATES OF IMIDAZOLIDONE DERIVA- TIVES AND POLYALKYLENE GLYCOL USE- FUL FOR IMPROVING TEXTILE MATERIALS Shigeru Tajima, Ashiya-shi, Katsumi Kobayashi, Toyonaka-shi, Hiroshi Fukuhara, Osaka, Hiroki Yamamoto, Takarazuka-shi, and Shigeru Ura, Nishinomiya-shi, Japan, assignors to Sumitomo Chemical Company, Ltd., Osaka, Japan No Drawing. Filed Mar. 11, 1969, Ser. No. 806,284 Claims priority, application Japan, Mar. 14, 1968, 43/ 16,919 Int. Cl. C07d 49/34 U.S. Cl. 260309.7 Claims ABSTRACT OF THE DISCLOSURE Novel composition of matter is produced by reacting 1 mole of alkylated derivatives of 4,5-bis-hydroxy-1,3-bishydroxymethyl-imidazolidone-2 of the formula,

wherein R R R and R respectively represent hydrogen or alkyl having 1 to 4 carbon atoms and at least one member of R R R and R is the said alkyl, with 0.2 to 2 moles of a water-soluble polyalkylene glycol having a molecular weight of 400 to 10,000.

This composition of matter is useful for improving hydrophobic synthetic textile materials or blends of hydrophobic synthetic fibers and cellulosic fibers.

The present invention relates to novel processes for the manufacture of a composition of matter and the resulting composition of matter. Further, the present invention pertains to processes for improvng textiles by impregnation with said composition and textiles resulting from said processes.

In general, polyester fibers and their blends are hydrophobic and have disadvantages such as a lack of hydrophilic property, an easy soiling in wear or an insufficient soil-removal by washing.

It is important to overcome these disadvantages, and a number of processes have been proposed in order to remove said drawbacks from textiles. For example, it has been known to give a soil-releasing property to synthetic textiles such as polyester textile by treating them with polyalkylene glycol such as polyethylene glycol. However, a low reactivity of the synthetic textile such as polyester textiles makes it difficult to improve the soil-releasing property with sufiicient durability. On the other hand, there has heretofore been known a process for improving hydrophobic synthetic textiles or mixed spun textiles of hydrophobic synthetic fibers and cellulosic fibers by treating them with a composition of matter comprising urea, formaldehyde and glyoxal (for example, US. Pat. No 3,049,446). However, the use of said composition of matter has given no satisfactory soil-releasing property.

The present inventors have found that a crease resistance and a soli-releasing property of hydrophobic synthetic textiles are brought about by treating the hydrophobic synthetic textiles with a compound having both a group having an afiinity to the hydrophobic synthetic textiles and a group capable of reforming drawbacks of hydrophobic synthetic textiles without imparing excellent intrinsic properties of the synthetic textiles. Further, the present inventors have found that a condensate obtained "Ice by an ester exchange reaction of alkylated compound of 4,5 bis-hydroxy-1,3-bis-hydroxymethyl-imidazolidone-Z and a water-soluble polyalkylene glycol is remarkedly suitable for the purpose.

Accordingly, one object of the present invention is to provide a process for preparing a composition of matter which is a condensate of a water-soluble polyalkylene glycol and alkylated compound of 4,5-bis-hydroxyl-1,3-bishydroxymethyl-imidazolidone-Z.

Another object of the present invention is to provide a composition of matter obtained by the process described above.

A further object of the present invention is to provide a process for improving properties of hydrophobic synthetic textiles or mixed spun textiles of the hydrophobic synthetic fibers and cellulosic fibers with the use of said composition of matter.

A still further object of the present invention is to provide improved hydrophobic synthetic textiles or mixed spun textiles of hydrophobic synthetic fibers and cellulosic fibers which have excellent crease resisting and soilreleasing properties.

Other objects and further scope of applicability of the present invention will become apparent from the detailed description given hereinbelow. It should be un-- derstood, however, that the detailed description and specific example-s are given by way of illustration only, Whose various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.

In order to accomplish these objects, the present invention provides a process for preparing a novel composition of matter, which comprises reacting 1 mole of alkylated compound of 4,5-bis-hydroxy-1,3-bis-hydroxymethyl-imidazolidone-2 represented by the formula,

0 II R1OCH2III N-CH1OR4 CH- H the 6R:

wherein R R 3 and R represent respectively hydrogen or alkyl having 1 to 4 carbon atoms and at least one group of R R R and R is the said alkyl, with 0.2 to 2 moles of a water-soluble polyalkylene glycol having a molecular weight of 400 to 10,000.

Further, the present invention provides a composition of matter obtained according to the above-mentioned process.

Further, the present invention provides a process for improving properties of hydrophobic synthetic textiles or mixed spun textiles of hydrophobic synthetic fibers and cellulosie fibers, which comprises impregnating the textiles with an aqueous solution containing said composition of matter and an acidic catalyst, squeezing the impregnated textiles, an amount of the composition of matter remained on the squeezed textiles being 0.5 to 10% by weight of the textiles, drying the squeezed textiles at a temperature of C. or below, and curing the dried textiles at a temperature of to C.

The alkylated compound of 4,5-bis-hydroxy-l,3-bishydroxymethyl-imidazolidone-Z is a known compound, and is produced by reacting, in the presence or absence of a solvent, urea, formaldehyde, glyoxal and a lower aliphatic alcohol having 1 to 4 carbon atoms. The lower alcohol is represented by the general formula R OH, R OH, R OH or R OH, among which methanol is preferable from the industrial and economical points of view. Only one kind or 2 to 4 kinds in combination of said 4 kinds of the alcohols may be used. Examples of the solvent include water, same alcohol as used as the reactant or a mixture thereof.

The foregoing reaction is carried out concretely by (l) Reacting urea, glyoxal, formaldehyde and a lower aliphatic alcohol having 1 to 4 carbon atoms in a single step, or

(2) Reacting 4,5-bis-hydroxy-imidazolidone-2 obtained by reacting urea with glyoxal, with a lower aliphatic alcohol having 1 to 4 carbon atoms, and then reacting the resultant material with formaldehyde, or

(3) Reacting 4,S-bis-hydroxy-imidazolidone-2 obtained by reacting urea with glyoxal, with formaldehyde, and then reacting the resultant material with a lower aliphatic alcohol having 1 to 4 carbon atoms, or

(4) Reacting 4,5-bis-hydroxy-imidazolidone-2 obtained by reacting urea with glyoxal, with formaldehyde and a lower aliphatic alcohol having 1 to 4 carbon atoms in a single step, or

(5) Reacting N,N-bis-hydroxymetl1yl-urea or an initial condensate thereof obtained by reacting urea with formaldehyde, with glyoxal, and then reacting the resultant material with a lower aliphatic alcohol having 1 to 4 carbon atoms, or

(6) Reacting N,N'-bis-hydroxymethyl-urea or an initial condensate thereof obtained by reacting urea with formaldehyde, with a lower aliphatic alcohol having 1 to 4 carbon atoms, and then reacting the resultant material with glyoxal, or

(7) Reacting an alkylated N,N-bis-hydroxymethylurea or an initial condensate thereof obtained by reacting urea, formaldehyde and a lower aliphatic alcohol having 1 to 4 carbon atoms in a single step, with glyoxal, or

(8) Reacting urea, glyoxal and formaldehyde in a single step, and then reacting the resultant material with a lower aliphatic alcohol having 1 to 4 carbon atoms, or

(9) Reacting the resultant product obtained in accordance with any of the foregoing processes of (l) to (8), with a lower aliphatic alcohol having 1 to 4 carbon atoms.

Water-soluble polyalkylene glycols used in the present invention include polyethylene glycol, polypropylene glycol, a copolymer consisting of ethylene glycol and propylene glycol.

The reaction or production of the present composition of matter is carried out in the presence of an acid. Examples of the acid are p-toluene sulfonic acid, toluene- 2,4-disulfonic acid, sulfuric acid, nitric acid, hydrochloric acid and phosphoric acid. Employment of a solvent is not critical in the reaction, however, employment of water is advantageous in the economical point of view. The reaction temperature is within a range of 20 to 100 C.

The composition of matter thus produced is soluble in water, and the resultant aqueous solution can be used for the treatment of improving the textiles.

The textiles referred to in the present invention are hydrophobic synthetic textiles, preferably polyester textiles, and mixed spun textiles of hydrophobic synthetic fibers and cellulosic fibers.

In accordance with the present invention, the treatment of the textiles is carried out by impregnating the textile in an aqueous solution at the first time. Concentration of the composition of matter in the aqueous solution is 0.1 to 20% (weight), preferably 1 to 10% (weight).

The acidic catalysts are used in the improvement of the present invention. The catalysts may be an organic acid, an inorganic acid or a salt of a strong acid and a weak base which is generally used for a resinous processing. Examples thereof include zinc nitrate, magnesium chloride, diammonium hydrogen phosphate, ammonium chloride, mineral acid salts of 2-amino-2-methyl propanol and ethanol amine, oxalic acid, maleic acid and the like, among which zinc nitrate or magnesium chloride is preferable. Said catalyst is used in an amount of 1 to 100% by weight, preferably 5 to 50% by weight of the composition of matter.

The impregnation is carried out at a room temperature.

In an aqueous solution in the present process, an assistant usually used may be added. Examples of the assistants include methylol urea, dimethylol ethylene urea, dimethyloluron, dimethylol triazone, dimethylol glyoxal :rnono-urein, dimethylol propylene urea and an alkylated compound thereof. The use of one kind or the combined use of two kinds of these assistants gives an effect further excellent in durability to textiles. The ratio of said assistant to the composition of matter may be 20% by weight or more.

The impregnated textile is then squeezed to remove excess solution and provide the desired amount of pick-up. In the present invention, a rate of the squeezing should be controlled in such a manner that an amount of pickup to the textile of the composition of matter is 0.5 to 10% by weight of textile.

Subsequently, the impregnated textile is dried, followed by curing, or if required, the drying and curing can be performed at the same time. The drying is caried out at a temperature of C. or below and requires about 1 to 10 minutes. At the next time, the dried textiles are cured. The curing is carried out at a temperature of to C. and requires usually about 30 sec. to 5 min. As the result, the composition of matter is converted to an insoluble material.

The textiles improved by the present invention have an increased hydrophilic property, a re-soil resistance and a soil releasing property due to a polyalkylene glycol chain. Further, the present composition of matter gives a large aflinity to hydrophobic synthetic fibers such as polyester fibers and the like due to an imidazolidone ring, and has an execellent durability due to reactivity with cellulosic fibers. Furthermore, in the case where there are many hydroxymethyl groups in the composition of matter, an improved crease resistance of the treated textile can be obtained.

The following exampes are given merely as illustrative of the present invention and are not intended to limit the present invention.

EXAMPLE 1 4,5-bis (methoxy)-imidazolidone-2 obtained by methylating 4,5-bis (hydroxy)-imidazolidone-2 was methylolated to 1,3-bis-(hydroxymethyl) 4,5 bis-(methoxymethyl)-imidazolidone-2. To a mixture of 62 g. of the resultant compound and g. of polyethylene glycol having a molecular weight of 600 was added 1.2 g. of para-toluene sulfonic acid, and heated at 60 C. for 40 minutes under a reduced pressure of about 50 mm. Hg. An amount of distilled methanol was 14.5 g. which corresponded to about 75% of the theoretical value. The resultant material was immediately diluted with water and neutralized with a 5 N aqueous sodium hydroxide solution to obtain 450 g. of a 50% aqueous solution.

The resultant solution was a light-yellowed transparent and viscous solution.

EXAMPLE 2 Reaction of 2.5 moles of 37% formalin, 1.0 mole of 40% glyoxal, 1.0 mole of urea and 5 moles of isopropanol gave an isopropylated compound of 1,3-bis-hydroxymethy1-4,5-bis-hydroxyimidazolidone-2 having 1.7 moles of isopropoxy group. To a mixture of 57 g. of an isopropylated compound of 1,3-bis-(hydroxymethyl)-4,5-bis-(hydroxy)- imidazolidone-2 and 300 g. of molten polyethylene glycol having a molecular weight of 2,000 Was added 0.5 ml. of cone. hydrochloric acid and heated with stirring at 60 C. for one hour. To the resultant solution was added 50 ml. of water, then 1.2 ml. of a 5 N aqueous sodium hydroxide solution was added thereto to neutralize the solution and thereafter 50 ml. of distillate were taken out under a reduced pressure. An amount of isopropanol in the distillate was 10 g., which corresponded to 56% of the theoretical amount. The resultant product was a compound wherein imidazolidone rings were bonded to both the terminals of polyethylene glycol.

EXAMPLE 3 Test items Re-soll resistance:

Reflection rate:

Dr 3 Degree of crease resistance (W-l-F) EXAMPLE 4 1,3-bis-(methoxymethyl) 4,5-bis-(hydroxy)-imidazolidone-2 used in Example 3 was reacted with an excessive amount of methanol to obtain a methylated compound of 1,3-bis-(hydaroxymethyl)-4,5 bis-(hydroxy)- imidazolidone-Z having a methylation degree of 3.5. 45.5 g. of the resultant methylated compound was reacted with 320 g. of a polyethylene glycol-polypropylene glycol copolymer (50% of polyethylene glycol, 50% of polypropylene glycol) having a molecular weight of 800, in a manner similar to that of Example 3. An amount of the distilled methanol was 18 g. which corresponded to 80% of the theoretical amount. The resultant product was a viscous solution capable of being optionally mixed with water.

EXAMPLE Urea, 40% glyoxal and 37% formalin were mixed in a molar ratio of 1.0:1.0':2.5 respectively, and the resultant mixture was reacted at pH of 7.0 to 7.5 at 60 C. for 3 hours, and then the reaction product was dehydrated and concentrated up to 90% of a solid. 10.0 moles of methanol was added to the resultant solid, and the resultant mixture was reacted at a pH of 2.0 at C. for one hour, to obtain an initial condensate of urea, glyoxal, formaldehyde and methanol having a methyla tion degree of 1.5. 50 g. of an 80% aqueous solution of the resultant condensate was mixed with 300 g. of polyethylene glycol having a molecular weight of 1,500, and to the resultant mixture was added 0.5 ml. of 70% sulfuric acid and reacted at 7 0 C. for one hour. The re action rate was measured from the produced methanol to be approximately 80%.

EXAMPLE 6 lMlXtlllC of 4,5-bis-(hydroxy)-imidazolidone-2, 37% formalin and methanol of a molar ratio of 1. 0:2.5 25.0 was heated at a pH of 5.2 for 90 minutes under a reflux condition to obtain an initial condensate of CH O/N =0.55. A procedure similar to that of Example 5 was repeated, except that 41 g. of a 95% aqueous solution of the resultant condensate was used in the place of the initial condensate of the Example 5 to give the product at an ether interchange reaction rate of 73%.

Non-treated EXAMPLE 7 A 50% aqueous solution of each composition of matter obtained respectively in Examples 1, 2 and 3 was prepared. A Tetoron-cotton (65/35) broadcloth was dipped into 100 ml. of a bath containing water and 15 g. of said 50% aqueous solution of resin and 4.5 g. of 30% aqueous solution of magnesium chloride, squeezed by a mangle so as to maintain an amount of pick-up of the composition of matter at 7.0% per an amount of the cloth, then dried at C. for 2 minutes, and thereafter cured at 160 C. for 3 minutes. Subsequently, after effecting home laundering of one to three times, a re-soil resistance property of the treated cloth was tested. Further, a degree of crease resistance of the resultant cloth was measured. As shown in Table 1, the results indicate conspicuously favourable durability and re-soil resistance and bring about an improvement in the degree of crease resistance.

TABLE 1 Treated cloth Cloth treated by composition in Example 3 Cloth treated by ST precl h scription Remarks:

(1) The ST prescription referred to herein means a case where 1,3-bis-(hydroxymethyl) 4,5 bis-(hyd1'oxy)- imidazolidone-Z is used in place of the composition of matter of the present invention.

(2) A method for testing a re-soil resistancen (a) Artificial oily soil: A mixture consisting of 12.5% (all percent: by weight) of stearic acid, 12.5% of oleic acid, 12.5% of coconut hardened oil, 12.5% of olive oil, 8.5% of cetyl alcohol, 21.5% of solid parafiin, 5.0% of cholesterol and '15.0% of carbon black.

(b) Artificial solid soil: A mixture consisting of 55% of clay, 17% of silicic anhydride, 0.5% of ferric oxide, 17% of portland cement, 8.75% of n-heptame and 1.75% of carbon black.

3 parts of a mixture composed of the artificial oily soil (3) Degree of soil redeposition o-Rs 1(01' Rs 3) D8 1 (or D8 3 R0 x R0: A reflection rate of the treated cloth prior to soiling.

Rs: A reflection rate of the treated cloth after soiling.

Rs 1 and Rs 3: Reflection rates of the treated cloths which were subjected to home launderings of '1 and 3 times respectively and then treated with soiling.

Test Method of Crease Resistance:

Monsanto Method (JIS 'L-1041 C Method) (W-l-F): (Warp-i-Filling recovery angle) (degree) 7 EXAMPLE 8 A bath (100 ml.) was prepared from 8 g. of the composition of matter obtained in (Example 2, .15 g. of a 50% aqueous solution of 4,5bis-(hydroxy)1,3-(hydroxymethyl)-imidazolidone-2 and 4.5 g. of a 30% aqueous solution of magnesium chloride with an addition of water. A Tetoron-cotton (65/35) broadcloth was dipped into the resultant bath, squeezed by a mangle to maintain an amount of pick-up of the composition of matter at 7.0% per an amount of the cloth, dried at 80 C. for 2 minutes and then cured at 160 C. for 3 minutes. A re-soil resistance and a rigidity of the cloth thus treated were measured, the result of which is shown in Table 2.

TABLE 2 Treated cloth Non- Cloth treated Cloth treated in treated by ST preaccordance with Test items cloth scription this example Degree of soil redeposition,

percei Dsl 25.0 26.0 6. D s 3 23. 5 25. 0 6. b Rigidity (g./20 mm.) 89 100 93 Remarks:

(1) The cloth treated by ST prescription referred to herein means one which is treated with 4,5-bis-(hydroxy) -1,3-bis- (hydroxymethyl -imidazolidone-2 alone according to the treatment of the present example.

(2) The rigidity was measured by means of a handle-ometer made by Thwing Albert Instrument Co.

From the foregoing Table 2, it is found that a re-soil resistance with a superior durability is obtained by the combined use of a prior known processing agent with the composition of matter obtained in Example 2 without being influenced badly on a feeling in touch.

The composition of matter obtained in Example 5 also showed favourable performances in the similar degree to that obtained in Example 2.

EXAMPLE 9 The composition of matter obtained in Example 3 was used in combination with a prescribed agent for a permanent press processing. A processing with the use of said combination was carried out just in the same manner as in Example 8. The result is shown in Table 3.

Remark:

(1) The motor-oil releasing property referred to herein means a soil releasing property when a drop of motoroil (made by Maruzen Sekiyu K.K., No. 40) is attached on a cloth and the resultant cloth is subjected to one time of home laundering. A degree of releasing property was judged on the following standard:

1: not entirely released. 2: somewhat released. 3: released ordinarily. 4: almost completely released. 5: completely released.

From the foregoing table, it is found that the combined use of the present composition of matter with the prescribed agent for the permanent press processing shows a favourable re-soil resistance and a motor-oil releasing property without influencing badly on a W & W property (wash and Wear property) and a feeling in touch (rigidity) of permanent press-processed cloth.

What we claim is 1. A process for preparing a novel composition of matter, which comprises reacting 1 mole of an alkylated compound of 4,5-bis-hydroxy-1,3-bis-hydroxymethylimidazolidone-2 represented by the formula,

0 C R1OCHZN/ \NCH2OR4 (JH('JE 0R 0R wherein R R R and R respectively represent hydrogen or alkyl having 1 to 4 carbon atoms, at least one group of R R R and R being the said alkyl, with 0.2 to 2 moles of a water-soluble polyalkylene glycol having a molecular weight of 400 to 10,000, wherein the reaction is carried out in the presence of an acid at a temperature of 20 C. to C.

2. A process according to claim 1, wherein the alkyl of R R R or R is methyl.

3. A process according to claim 1, wherein the Watersoluble polyalkylene glycol is polyethylene glycol, polypropylene glycol or a copolymer consisting of ethylene glycol and propylene glycol.

4. A process according to claim 1, wherein the acid is p-toluene sulfonic acid, toluene-2,4-disulfonic acid, hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid.

5. A composition of matter produced according to a process as claimed in claim 1.

References Cited UNITED STATES PATENTS 3,029,164 4/1962 Seki et a1 260309.7 3,427,121 2/1969 Frick et a1. 81l5.6

OTHER REFERENCES Harper et al. Textile Research Journal, vol. 38, No. (3) pp. 292-304, March 1968.

HENRY R. JILES, Primary Examiner R. T. BOND, Assistant Examiner US. Cl. X.R. 117-4395, 138.8

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,652,583 r Dated April '28, 1972 Inventor(s') Shigeru Taj ima et a1.

It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

In column liafter line 12, please insert the following missing claim for priority:

-Ja'panese ApplnrNor' 28l88-filedApril 26, 1968-- Signed and sealed this 17th day of October 1972.

(SEAL) Attest:

.EDWARD M.FLETCHER,JR. ROBERT GOTTSCHALK Attesting Officer Commissioner of Patents "ORM PO-OSO (10-69) USCOMM-DC 60376-P69 h as GOVERNMENT rmm'ms OFFICE: I969 o ns-:3!

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 652,583 Dated April 1972 Inventor(s) Shigeru Taj ima et a1.

It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

In column 1, I after line 12, please insert the following missing claim for priority:

-Japanese Appln. No. 28188- filed April 26, 1968-- Signed and sealed this 17th day of October 1972.

(SEAL) Attest:

EDWARD M.FLETCHER,JR. ROBERT GOTTSCHALK Attesting Officer Commissioner of Patents 'ORM PO-IOSO (10-69) USCOMM-DC 603764- 09 w us. GOVERNMENT rmm'mc OFFICE: I969 0-J66-.\J4

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3896088 *Nov 24, 1972Jul 22, 1975Du PontFluorinated oily soil release agents
US3907736 *May 20, 1974Sep 23, 1975Eastman Kodak CoFinishing agents for textiles
US3960983 *Dec 6, 1974Jun 1, 1976American Cyanamid CompanyCoating, lamination, molding materials, adhesives
US4284536 *Jun 23, 1980Aug 18, 1981American Cyanamid Co.Imidazolidinone additive
US4295846 *Mar 18, 1980Oct 20, 1981Basf AktiengesellschaftProcess for the production of formaldehyde-free finishing agents for cellulosic textiles and the use of such agents
US6153762 *Jul 31, 1997Nov 28, 2000Basf AktiengesellschaftBridged bis-4,5-dihydroxyimidazolidin-2-ones, n-methylolated derivatives thereof, their preparation and crosslinking textiles therewith
US6861520 *Apr 30, 2003Mar 1, 2005Dan River, Inc.The textiles formed by such a process can comprise an article of clothing adapted to trap odors emanating from a wearer
US7714065 *Nov 15, 2004May 11, 2010The Procter & Gamble CompanyAqueous mixture comprising a hydroxyl polymer, a hydrophile/lipophile system comprising a hydrophilic component and a lipophilic component, and a crosslinking system comprising a crosslinking agent,wherein hydrophilic component facilitates dispersibility of lipophilic components in aqueous mixture
US8071203Mar 25, 2010Dec 6, 2011The Procter & Gamble CompanyPolymeric structures comprising a hydrophile/lipophile system
US8137797May 19, 2011Mar 20, 2012The Procter & Gamble CompanyPolymeric structures comprising a hydrophile
US8241738Feb 13, 2012Aug 14, 2012The Procter & Gamble CompanyPolymeric structures comprising a sulfosuccinate
US8445100Jul 3, 2012May 21, 2013The Procter & Gamble CompanyPolymeric structures comprising a sulfosuccinate
US8709585May 20, 2013Apr 29, 2014The Procter & Gamble CompanyPolymeric structures comprising a siloxane
EP0042478A1 *Apr 27, 1981Dec 30, 1981American Cyanamid CompanyMethod for the adhesion of rubber to reinforcing materials
Classifications
U.S. Classification548/317.5, 525/517
International ClassificationC07D233/40, C08G65/333
Cooperative ClassificationC07D233/40, C08G65/33396
European ClassificationC08G65/333U, C07D233/40