Aqueous dispersion of polyurethane resin, flame-retardant polyester fiber using the same, and method for producing said fiber

Patent metadata

Field	Value
Publication number	US-9834884-B2
Application number	US-201314429855-A
Country	US
Kind code	B2
Filing date	Sep 19, 2013
Priority date	Sep 21, 2012
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

An aqueous dispersion of polyurethane resin is obtained by a chain elongation reaction in water wherein (C) at least one chain extender selected from a group consisting of water-soluble polyamines, hydrazine and derivatives thereof is added to a dispersion liquid obtained by emulsifying and dispersing a mixture in water. The mixture comprises: (B) at least one compound selected from the phosphorous compounds represented by the following formula (1) and (A) an urethane prepolymer and/or a neutralized urethane prepolymer material which has an isocyanate group at the terminal. The urethane prepolymer of component (A) is an urethane prepolymer obtained from (a1) an organic polyisocyanate and (a2) a polymeric polyol. The neutralized urethane prepolymer material of component (A) is a neutralized material obtained by neutralizing an urethane prepolymer which is obtained by further using (a3) a compound having an anionic hydrophilic group and at least two active hydrogens in a molecule together with the components (a1) and (a2).

First claim

The invention claimed is:

1. An aqueous dispersion of polyurethane resin obtained by
a chain elongation reaction in water, by adding (C) at least one chain extender selected from a group consisting of water-soluble polyamines, hydrazine and derivatives thereof to a dispersion liquid obtained by emulsifying and dispersing a mixture in water,
said mixture comprising (B) at least one compound selected from the phosphorous compounds represented by the following formula (1) and (A) an urethane prepolymer and/or a neutralized urethane prepolymer material which has an isocyanate group at the terminal,
wherein said urethane prepolymer of said component (A) is an urethane prepolymer obtained by reacting (a1) an organic polyisocyanate and (a2) a polymeric polyol, and said neutralized urethane prepolymer material is a neutralized material obtained by neutralizing an urethane prepolymer which is obtained by further using (a3) compound having an anionic hydrophilic group and at least two active hydrogens in a molecule together with said components (a1) and (a2)

wherein, n is a number from 2.6 to 10, A is a single bond, —C(CH 3 ) 2 —, —SO 2 -, —S—or —O—, R is each, independently a hydrogen atom, an alkyl group or a phenyl group,
wherein said polymeric polyol (a2) is selected from the group consisting of polycarbonate polyols, polyether polyols and dimerdiols, and
wherein said polyether polyols are obtained by:
(a) polymerizing one or more polyols selected from ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylol ethane, trimethylol propane, sorbitol, sucrose, bisphenol A, bisphenol S and hydrogenated bisphenol A, or
(b) addition polymerization reaction of compound having at least two active hydrogens and one or more monomers selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide, epichlorohydrin, tetrahydrofuran and cyclohexylene oxide.

2. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the organic polyisocyanate of said component (a1) is an aliphatic diisocyanate or an alicyclic diisocyanate.

3. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the polymeric polyol of said component (a2) is a polyol having 500 to 4000 of average molecular weight.

4. The aqueous dispersion of polyurethane resin according to claim 1 , wherein said component (A) is an urethane prepolymer and/or a neutralized urethane prepolymer material obtained by further adding a polyalcohol as a component (a4) together with said components from (a1) to (a3).

5. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the content of phosphorous compound of said component (B) is 1 to 15 parts by mass relative to 100 parts by mass of polyurethane resin in said aqueous dispersion of polyurethane resin.

6. The aqueous dispersion of polyurethane resin according to claim 1 , wherein said component (A) is a neutralized urethane prepolymer material and the anionic hydrophilic group of the compound (a3), which is one of the elements constituting said neutralizing material, is a carboxyl group.

7. A flame retardant polyester fiber obtained by providing the process liquid containing the aqueous dispersion of polyurethane resin according to claim 1 to the polyester fiber and then drying.

8. The flame retardant polyester fiber according to claim 7 , wherein the provided amount of the phosphorous compound (B) is 0.1 to 2 parts by mass relative to 100 parts by mass of said polyester fiber.

9. A method for manufacturing the flame-retardant polyester fiber comprising a step of providing the process liquid containing the aqueous dispersion of polyurethane resin according to claim 1 to the surface of polyester fiber so that the provided amount of the phosphorous compound (B) is 0.1 to 2 parts by mass relative to 100 parts by mass of said polyester fiber, and a step of drying it.

10. The aqueous dispersion of polyurethane resin according to claim 1 , wherein said polymeric polyol (a2) is a polycarbonate polyol.

11. The aqueous dispersion of polyurethane resin according to claim 10 , wherein polycarbonate polyol is polyhexamethylene carbonatediol or 3-methyl-1,5-pentanediol carbonatediol.

12. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the (a1) organic polyisocyanate is isophorone diisocyanate or dicyclohexylmethane diisocyanate.

13. The aqueous dispersion of polyurethane resin according to claim 1 , wherein said phosphorous compound of component (B) is one or more compounds selected from the following phosphorous compounds from (1) to (4):

14. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the content of phosphorous compound of component (B) is 1 to 30 parts by mass relative to 100 parts by mass of polyurethane resin in said aqueous dispersion of polyurethane resin.

15. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the content of phosphorous compound of component (B) is 3 to 15 parts by mass relative to 100 parts by mass of polyurethane resin in said aqueous dispersion of polyurethane resin.

16. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the chain extender of component (C) is ethylene diamine, propylene diamine, tetramethylene diamine, hexamethylene diamine, diaminocyclohexyl methane, hydrazine, piperazine, 2-methylpiperazine, tolylenediamine, xylylene diamine, isophorone diamine, norbornane diamine, diethylene triamine, triethylene tetramine.

17. The aqueous dispersion of polyurethane resin according to claim 1 , wherein the chain extender of component (C) is 1,1′-ethylene dihydrazine, 1,1′-trimethylene dihydrazine, 1,1′ -(1,4-butylene)dihydrazine, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, sebacic acid dihydrazide, maleic acid dihydrazide, fumaric acid dihydrazide or itaconic acid dihydrazide.

Assignees

• Adeka Corp

Inventors

• Shimamura Nobuyuki
• Usui Takashi

Classifications

• C08G18/4854

  Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group · CPC title

• C08G18/6659

  with compounds of group C08G18/34 · CPC title

• D06M2101/32

  Polyesters · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• D06M15/564

  Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them · CPC title