Cross-linked polymers, methods for their manufacture, and use

Abstract

Polymers bearing the following structural elements per molecule: (A) an average of at least two alkoxylated (poly)alkylenimine units, said alkylene being selected from C.sub.2-C.sub.10-alkylene and said alkoxylation being selected from ethoxylation, propoxylation, butoxylation and combinations of at least two of the foregoing, (B) at least one polysiloxane unit, and (C) at least one linkage connecting at least two different alkoxylated (poly)alkylenimine units (A) bearing at least one polysiloxane unit (B), each link-age (C) being selected from organic spacers bearing in the range of from 4 to 30 carbon atoms.

Claims

1. A polymer bearing the following structural elements per molecule: (A) an average of at least two alkoxylated (poly)alkylenimine units, said alkylene being selected from C.sub.2-C.sub.10-alkylene and said alkoxylation being selected from ethoxylation, propoxylation, butoxylation and combinations of at least two of the foregoing, (B) at least one polysiloxane unit, and (C) at least one linkage connecting at least two different alkoxylated (poly)alkylenimine units (A) bearing at least one polysiloxane unit (B), each linkage (C) being selected from organic spacers bearing in the range of from 4 to 30 carbon atoms.

2. The polymer according to claim 1 wherein such alkoxylated (poly)alkylenimine (A) is selected from poly-ethoxylated polyethylenimine, ethoxylated polypropylenimine, ethoxylated polyhexanamines, ethoxylated and propoxylated polyethylenimine, ethoxylated and propoxylated polypropylenimine, and ethoxylated and poly-propoxylated ,-hexanediamines.

3. The polymer according to claim 1 having an average molecular weight M.sub.w in the range of from 2,500 to 1,500,000 g/mol.

4. The polymer according to claim 1 wherein linkage (C) is selected from a diester spacer and a diurethane spacer.

5. The polymer according to claim 1 wherein the polydispersity Q of polyalkoxylated (poly)alkylenimine (A) is in the range of from 2 to 15.

6. The polymer according to claim 1 wherein linkage (C) is selected from a terephthalic acid diester linkage, an isophthalic acid diester linkage, an adipic acid diester linkage, a cyclohexanedicarboxylic acid diester linkage, and a diurethane linkage based on toluylene diisocyanate, hexamethylene diisocyanate, and (4,4-diisocyanatophenyl)methylene.

7. The polymer according to claim 1 wherein said polysiloxane unit (B) bears at least 10 OSi(R.sup.1R.sup.2)- units, with R.sup.1 and R.sup.2 being different or identical and selected from C.sub.1-C.sub.10-alkyl, phenyl, benzyl and C.sub.5-C.sub.8-cycloalkyl.

8. The polymer according to claim 1 containing an average in the range of from 3 to 15 alkoxylated (poly)alkylenimine units (A) per molecule.

9. A process for making a polymer according to claim 1, said process comprising (a) providing an alkoxylated (poly)alkylenimine (A), (b) reacting said alkoxylated (poly)alkylenimine (A) with at least one ,-dihydroxy polysiloxane, and (c) reacting the product according to step (b) with at least one compound bearing at least two functional groups per molecule that are reactive towards alkanol groups.

10. The process according to claim 9 wherein said compound bearing at least two functional groups per molecule is selected from terephthalic acid dimethyl ester, terephthalic acid diethyl ester, isophthalic acid dimethyl ester, isophthalic acid diethyl ester, cyclohexanedicarboxylic acid dimethyl ester, cyclohexanedicarboxylic acid diethyl ester, toluylene diisocyanate, hexamethylene diisocyanate, and 4,4-methylenebis(phenyl isocyanate).

11. The process according to claim 9 wherein step (c) is performed in the presence of a catalyst.

12. A method for the manufacture of a leather or textile comprising treating a semi-finished product tanned with a chrome tanning agent, a mineral tanning agent, a polymer tanning agent, an aldehyde, a syntan, or resin tanning agent with a polymer according to claim 1.

13. A method of coating concrete or bricks comprising applying a polymer according to claim 1 to the concrete or bricks.

14. A method for the manufacture of a textile comprising treating the textile with a polymer according to claim 1.

Description

WORKING EXAMPLES

(1) General remarks:

(2) Percentages refer to % by weight unless specifically defined otherwise.

(3) I. Manufacture of polyethylenimines

(4) I.1 Synthesis by polymerization

(5) General remarks: the syntheses were performed in a continuously operated tubular reactor, length 18 m, inner diameter 3.5 mm. Said tubular reactor had two reaction zones. In the first reaction zone the temperature was kept at 125 to 130 C., in the second at 150 C. The first reaction zone was in the first 12 m, the second reaction zone in the remaining 6 m of the tubular reactor. The pressure was kept at 0.5 bar above the pressure necessary to keep the reaction mixture liquid, which requires a minimum of 1.5 bar.

(6) Step (a1) was performed in a so-called mixing chamber, in which water, ethylenimine, aqueous CO.sub.2 solution, and ethylenediamine were mixed through three static mixers. The mixture so obtained was then transferred into the tubular reactor.

(7) The following starting materials were used:

(8) Aziridine, provided as 25 wt. % aqueous solution

(9) CO.sub.2 as 2.5 wt. % aqueous solution

(10) 1,2-ethylenediamine

(11) I.1.1 Synthesis of polyethylenimine (PEI.1)

(12) A 2-litre reactor with plate heat exchanger, was charged with 88 g 1,2-ethylenediamine and 27 g CO.sub.2 (as dry ice). A 60% by weight aqueous solution of aziridine was fed at a rate of 270 g/h. Through exothermic primary polymerization the temperature rose to 140 C. The temperature was maintained at 140 C. In total, an amount of 980 g of the aziridine solution were added. After the addition had been completed the reaction mixture was stirred for another two hours at 145 C.

(13) Then the reaction was stopped by cooling to ambient temperature and pressure release. The water was removed, and polyethylenimine (PEI.1) was obtained.

(14) I.1.2 Synthesis of polyethylenimine (PEI.2)

(15) A premix was provided from CO.sub.2 as 2.5 wt. % aqueous solution and 1,2-ethylenediamine. The tubular reactor described above was fed with a 360 g/h 25 wt. % aqueous solution of aziridine and the above premix in a way that a feed resulted in the addition of 17 g/h 2.5 wt. % aqueous solution of CO.sub.2 and 6.2 g/h 1,2-ethylenediamine were introduced into the tubular reactor. The feed had a temperature of 5 C. at the time of mixing. Through exothermic primary polymerization the temperature rose to 80 to 160 C. when entering the first reaction zone. At the end of the tubular reactor, the pressure was adjusted to 5 bar. The conversion of aziridine in the tubular reactor was 99 mol-%.

(16) After having passed the tubular reactor, the reaction mixture was transferred into a semicontinuously operated tank reactor operated at 160 C. There, the polymerization was completed, step (a3). The average residence time was 2.5 hours in the stirred tank reactor hours. When the tank reactor was full the reaction was stopped by cooling to ambient temperature and pressure release. The water was removed, and polyethylenimine (PEI.2) was obtained.

(17) I.1.3 Synthesis of polyethylenimine (PEI.3)

(18) A 2-litre reactor with plate heat exchanger, was charged with 41.8 g 1,2-ethylenediamine and 14.2 g CO.sub.2 (as dry ice). A 60% by weight aqueous solution of aziridine was fed at a rate of 250 g/h. Through exothermic primary polymerization the temperature rose to 140 C. The temperature was maintained at 140 C. In total, an amount of 1 kg of the aziridine solution were added. After the addition had been completed the reaction mixture was stirred for another two hours at 145 C.

(19) Then the reaction was stopped by cooling to ambient temperature and pressure release. The water was removed, and polyethylenimine (PEI.3) was obtained.

(20) The polyethylenimines (PEI) provided are summarized in Table 1.

(21) TABLE-US-00001 TABLE 1 Polyethylenimines and their properties M.sub.w [g/mol] M.sub.n [g/mol] M.sub.w/M.sub.n Amine value (PEI.1) 880 620 1.42 20.5 (PEI.2) 28,000 6,800 4.1 15.3 (PEI.3) 2,000 1,150 1.74 17.3

(22) All molecular weights were determined by GPC with 1.5% by weight aqueous formic acid as eluent and cross-linked poly-hydroxyethylmethacrylate as stationary phase. Internal standard was a 0.05%by weight solution of tert.-butanol in 1.5% by weight aqueous formic acid. The column was calibrated with the help of pullulan (-1,4-;-1,6-glucan) samples with known molecular weight. In Table 1, the amine value is the primary amine value.

(23) II. Syntheses of alkoxylated polyethylenimines (A)

(24) II.1 Synthesis of mono-alkoxylates

(25) II.1.1 Synthesis of mono-ethoxylate 1

(26) A 2-I autoclave was charged with 645 g of polyethylenimine (PEI.1) and 32 g of water and then purged with nitrogen. Then, the autoclave was heated to 90 C. An amount of 595 g of ethylene oxide was added within 10 hours under stirring and allowed to react for additional 12 hours at 90 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,235 g of a highly viscous yellow liquid, mono-ethoxylate 1 was obtained.

(27) II.1.2 Synthesis of mono-propoxylate 2

(28) A 2-I autoclave was charged with 323 g of polyethylenimine (PEI.1) and 16 g of water and then purged with nitrogen. Then, the autoclave was heated to 90 C. An amount of 384 g of propylene oxide was added within 10 hours under stirring and allowed to react for additional 12 hours at 90 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 692 g of a highly viscous yellow liquid, mono-propoxylate 2 was obtained.

(29) II.1.3 Synthesis of mono-ethoxylate 3

(30) A 2-I autoclave was charged with 520 g of polyethylenimine (PEI.2) and 15.5 g of water and then purged with nitrogen. Then, the autoclave was heated to 90 C. An amount of 350 g of ethylene oxide was added within 10 hours under stirring and allowed to react for additional 12 hours at 90 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 859 g of a highly viscous yellow liquid, mono-ethoxylate 3 was obtained.

(31) II.1.4 Synthesis of mono-ethoxylate 4

(32) A 2-I autoclave was charged with 340 g of polyethylenimine (PEI.3) and 15.5 g of water and then purged with nitrogen. Then, the autoclave was heated to 90 C. An amount of 257 g of ethylene oxide was added within 10 hours under stirring and allowed to react for additional 12 hours at 90 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 601 g of a highly viscous yellow liquid, mono-ethoxylate 4 was obtained.

(33) II.1.5 Synthesis of mono-propoxylate 5

(34) A 2-I autoclave was charged with 280 g of polyethylenimine (PEI.3) and 12 g of water and then purged with nitrogen. Then, the autoclave was heated to 90 C. An amount of 278 g of propylene oxide was added within 10 hours under stirring and allowed to react for additional 12 hours at 90 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 551 g of a highly viscous yellow liquid, mono-propoxylate 5 was obtained.

(35) II.2 Alkoxylations

(36) II.2.1 Synthesis of alkoxylated polyethylenimine (A.1)

(37) A 2-I autoclave was charged with 330 g of mono-ethoxylate 1 and 5.6 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 780 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,106 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.1).

(38) II.2.2 Synthesis of alkoxylated polyethylenimine (A.2)

(39) A 2-I autoclave was charged with 105 g of mono-ethoxylate 1 and 2.0 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 998 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,100 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.2).

(40) II.2.3 Synthesis of alkoxylated polyethylenimine (A.3)

(41) A 2-I autoclave was charged with 152 g of mono-propoxylate 2 and 2.8 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 963 g of propylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,085 g of a light brown liquid was obtained that was alkoxylated polyethylenimine (A.3).

(42) II.2.4 Synthesis of alkoxylated polyethylenimine (A.4)

(43) A 2-I autoclave was charged with 124 g of mono-ethoxylate 1 and 2.7 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 530 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. Then, 618 g of propylene oxide were added under stirring within 12 hours and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,265 g of a yellow liquid was obtained that was alkoxylated polyethylenimine (A.4).

(44) II.2.5 Synthesis of alkoxylated polyethylenimine (A.5)

(45) A 2-I autoclave was charged with 76 g mono-ethoxylate 1 and 2.0 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 605 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. Then, 565 g of propylene oxide were added under stirring within 12 hours and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,244 g of a yellow liquid was obtained that was alkoxylated polyethylenimine (A.5).

(46) II.2.6 Synthesis of alkoxylated polyethylenimine (A.6)

(47) A 2-I autoclave was charged with 321 g of mono-ethoxylate 5 and 5.6 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 830 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,148 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.6).

(48) II.2.7 Synthesis of alkoxylated polyethylenimine (A.7)

(49) A 2-I autoclave was charged with 155 g of mono-ethoxylate 5 and 2.6 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 1,411 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,565 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.7).

(50) II.2.8 Synthesis of alkoxylated polyethylenimine (A.8)

(51) A 2-I autoclave was charged with 175 g of mono-propoxylate 6 and 2.9 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 1,338 g of propylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,512 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.8).

(52) II.2.9 Synthesis of alkoxylated polyethylenimine (A.9)

(53) A 2-I autoclave was charged with 290 g of mono-ethoxylate 3 and 5.3 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 680 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 979 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.9).

(54) II.2.10 Synthesis of alkoxylated polyethylenimine (A.10)

(55) A 2-I autoclave was charged with 185 g of mono-ethoxylate 3 and 3.9 g of a 50% by weight aqueous KOH solution. The water was removed at 20 mbar. Then, the autoclave was purged with nitrogen and subsequently heated to 120 C. Within 12 hours, 878 g of ethylene oxide were added under stirring and allowed to react for additional 12 hours at 120 C. The mixture so obtained was cooled to 80 C., and the volatile ingredients were removed in vacuo. An amount of 1,068 g of a light brown solid was obtained that was alkoxylated polyethylenimine (A.10).

(56) TABLE-US-00002 TABLE 2 Summary of properties of alkoxylated polyethylenimines (A.1) to (A.10) M.sub.n (A) Entry Amine AO moles AO/NH [g/mol] (A.1) PEI.1 EO 6 3,300 (A.2) PEI.1 EO 20 12,700 (A.3) PEI.1 PO 12 10,600 (A.4) PEI.1 EO, PO 10, 8 12,400 (A.5) PEI.1 EO, PO 18, 12 20,100 (A.6) PEI.3 EO 7 7,700 (A.7) PEI.3 EO 22 24,200 (A.8) PEI.3 PO 16 18,050 (A.9) PEI.2 EO 6 39.200 (A.10) PEI.2 EO 10 58.000 Explanations with respect to Table 2: AO: alkylene oxide, EO: ethylene oxide, PO: propylene oxide

(57) III. Crosslinking Reactions

(58) General procedure for urethane linking

(59) A four-necked 1-litre flask with stirrer, thermometer and condenser for distillation was charged with 200 g of (A) according to table 3 and heated to 35 C. 50 g of ethyl acetate and the appropriate amount of component (C) (see table 3) were added under stirring. Then a 50% solution of toluenediisocyanate (TDI) or hexamethylenediisocyanate (HMDI) according to Table 3 were added dropwise within 20 minutes (stirring). The temperature was increased to 120 C. within 30 minutes and the mixture was stirred at for another 90 minutes while ethyl acetate was distilled off. Then, 100 ml water were added at 90 C., the reaction mixture was stirred for 15 minutes and finally, volatile ingredients were removed by rotary evaporation at 60 C. and 10 mbar.

(60) TABLE-US-00003 TABLE 3 crosslinking reactions and properties of inventive polymers molar ,-hydroxy ratio average number polymer (B) (A) polysiloxane (A)/(B)/C of units A (P.1) TDI (A.1) 1 1/0.7/0.3 3.9 (P.2) HMDI (A.2) 1 1/0.6/0.3 3.1 (P.3) HMDI (A.3) 1 1/0.6/0.3 2.9 (P.4) TDI (A.4) 1 1/0.7/0.3 3.5 (P.5) TDI (A.4) 2 1/1/0.45 5.1 (P.6) TDI (A.5) 2 1/0.5/0.25 2.9 (P.7) TDI (A.5) 2 1/0.8/0.25 4.5 (P.8) TDI (A.6) 2 1/0.5/0.25 2.9 (P.9) TDI (A.6) 1 1/1/0.35 4.1 (P.10) TDI (A.7) 2 1/0.8/0.3 3.0 (P.11) DMT (A.8) 1 1/0.5/0.2 2.4 (P.12) DMT (A.9) 1 1/0.6/0.25 3.1 (P.13) DMT (A.10) 1 1/0.5/0.25 2.8 ,-dihydroxy polysiloxane 1: M.sub.n 2,500 g/mole, dynamic viscosity at 25 C.: 500 mPa .Math. s ,-dihydroxy polysiloxane 2: M.sub.n 5,000 g/mole, dynamic viscosity 25 C.: 2500 mPa .Math. s

(61) IV. Application Examples

(62) IV. 1 Retannage of leather, use in the retanning of leatherproduction of upper leather

(63) The data in % by weight are based in each case on the shaved weight, unless stated otherwise.

(64) Two commercial cattle wet-blues including flanks (from Packer, USA) were shaved to a thickness of 1.7 to 1.9 mm and cut into seven strips of about 700 g each. 1.5% by weight of sodium formate and 0.5% by weight of NaHCO.sub.3 and 1% by weight of a naphthalenesulfonic acid/formaldehyde condensate, prepared according to U.S. Pat. No. 5,186,846, example entitled Dispersant 1, were then added to the strips in a drum (50 I) and with a liquor length of 200% by weight with an interval of 10 minutes. After 70 minutes, the liquor was discharged. The strips were then distributed over 7 separate drums for drumming.

(65) Thereafter, as stated in table 4, 100% of water, 2% by weight of a 40% by weight solids content aqueous solution of polyacrylic acid, M.sub.n 70,000 g/mol, pH: 5.5, and 4% by weight of inventive polymer according to table 4 were added and the mixtures were drummed for 30 minutes. Thereafter, 2% by weight each of sulfone tanning agent from EP-B 0 459 168, example K1, and 3% by weight each of vegetable tanning agent Mimosa and 2% by weight each of a 40% strength by weight (solids content) aqueous solution of dyes, whose solids had the following composition, was metered into drums 1 to 7 at from 25 to 35 C.: 70 parts by weight of dye from EP-B 0 970 148, example 2.18, 30 parts by weight of Acid Brown 75 (iron complex), Colour Index 1.7.16,

(66) and drumming was effected for 30 minutes.

(67) Acidification was then effected with formic acid to a pH of 3.9 to 4.1 in several steps. After additional 20 minutes of drumming, the leathers were then washed with 200% by weight of water. Finally, 3% by weight of a fatliquoring agent, which was prepared as described under IV.2, were metered into 100% of water at 50 C. After a drumming time of 45 minutes, acidification to pH 3.7 was effected with 1% by weight of formic acid. The washed leathers so obtained were dried and staked.

(68) The leathers (L.1) to (L12) had excellent body, softness and handle in combination with outstanding dye penetration of the fibers.

(69) TABLE-US-00004 TABLE 2 Performance characteristics of leathers L.1 to L-12 and comparative leathers C-(L.6) and C-(L.7) Body Levelness Leather Copolymer Body Softness Grain tightness bend/flank Dye penetration of dyeing (L.1) (P.1) 1 2 1 1.5 1 2 (L.2) (P.2) 1.5 1.5 2 2.5 1.5 1 (L.5) (P.5) 2 1.5 1 1.5 1.5 1 (L.9) (P.9) 1.5 2 2 2 2 1.5 (L.12) (P.12) 1 2 1 1 2 2 C-(L.6) None 3 3.5 2.5 3 3 3.5 C-(L.7) (A.2) 2.5 2.5 2 3 2.5 2.5

(70) Remarks:

(71) The evaluation of body, grain tightness, softness, penetration and levelness of dyeing was effected according to a rating system from 1 (very good) to 5 (poor).

(72) IV. 2 Manufacture of a fatliquoring agent

(73) The following were mixed in a 2 I kettle:

(74) 230 g of a polyisobutene having M.sub.n=1 000 g/mol and M.sub.w=1 800 g/mol

(75) 30 g of n-C.sub.18H.sub.37O(CH.sub.2CH.sub.2).sub.25OH

(76) 5 g of n-C.sub.18H.sub.37O(CH.sub.2CH.sub.2O)80OH

(77) 40 g of oleic acid

(78) 230 g of sulfited oxidized triolein

(79) The mixture was heated to 60 C. with stirring, and 470 g of water and 10 g of n-C16H33O(CH.sub.2CH.sub.2O).sub.7OH were added. The resulting emulsion was then passed through a gap homogenizer. A finely divided, stable emulsion was obtained.

(80) V. Treatment of Textiles with Inventive Copolymers

(81) Parts refer to parts by weight unless specifically noted otherwise.

(82) All inventive polymers were self-dispersing in water. No additional surfactant was used for dispersing inventive polymers in water.

(83) The textiles were tested in accordance with ASTM Method D-1776-79, natural cotton. As test textiles, untreated terry towels from Mve Frottana Textil GmbH & Co. KG, D-02779 Groschnau, were used. Either 0.5% by weight or 1.0% by weight, see table 5, of inventive polymer as a were applied to a terry towel by padding, followed by drying for 3 hours at 40 to 50 C.

(84) For comparative purposes, an aminofunctional silicone according to U.S. Pat. No. 4,247,592, example 1, was emulsified with 3.6 parts n-C15-alkyl-(EO)15 and 2.4 parts n-C15-alkyl-(EO)3 and 12 parts water to form a premix. The premix was placed in the feeder and passed through a Homogenizer Type 15M from Manton-Graulin Mfg. Co., Inc. (Evert, Mass.) at 210 bar. Additional 48 parts of water were added slowly to the homogenizer feeder, and the resultant mixture was passed twice through the homogenizer at 210 bar. The emulsion contained 40 parts of aminopolysiloxane to 60 parts water. For the inventive species the preparation of a pre-emulsion is not necessary.

(85) Softness and/or amine-like hand evaluations were performed by a hand panel. For the softness evaluation, textiles were rated using a 1-to-10 scale on which scale, 1 was the softest and 10 was the harshest value.

(86) TABLE-US-00005 TABLE 5 Inventive polymers in textile treatment Softness Softness Touch Self dispersing textile polymer 0.5% 1.0% 1.0% yes/no Water takeup [s] T.1 (P.1) 4 3 silky Yes 8 T.2 (P.2) 2.5 1.5 silky Yes 6 T.4 (P.4) 3 2.5 silky Yes 9 T.5 (P.5) 4 3 silky Yes 7 T.6 (P.6) 4 3 silky Yes 7 T.8 (P.8) 4 3 silky Yes 8 T.9 (P.9) 3.5 3 silky Yes 8 T.10 (P.10) 4 3 silky Yes 8 T.11 (P.11) 3 2.5 slippery Yes 11 T.12 (P.12) 3 2.5 slippery Yes 12 C-T.13 (A.2) 7 7 rough No 10 C-T.14 U.S. Pat. No. 4,247,592 5.5 4.5 slippery No 17 C-T.15 none 8 8 rough 8 U.S. Pat. No. 4,247,592: refers to the polymer from U.S. Pat. No. 4,247,592, Ex. 1.