Stainproofing agent and process for its preparation

• US 4,504,401 A
• Filed: 08/08/1983
• Issued: 03/12/1985
• Est. Priority Date: 08/20/1982
• Status: Expired due to Term

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Hayashi, Takao, Oda, Yoshio, Matsuo, Masashi, Itoh, Katsuji
• Primary Examiner(s): Tungol, Maria Parrish
• Application Number:
  US06/521,407
• Time in Patent Office: 582 Days
• Field of Search: 252/8.8, 252/8.75
• US Class Current: 252/8.62
• CPC Class Codes: C07C 273/1809 with formation of the N-C(O)-N moiety
• CPC Class Codes: C07C 275/62 Y being a nitrogen atom, e.g. biuret
• CPC Class Codes: C07D 251/30 Only oxygen atoms
• CPC Class Codes: C07D 251/34 Cyanuric or isocyanuric esters
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: D06M 15/576 containing fluorine

Abstract

A stainproofing agent containing as an active ingredient a polyfluoroalkyl group-containing compound represented by the following general formula and having a molecular weight of from 800 to 3000:

(R.sub.f -X-A-CONH).sub.a W-NHCO-A'"'"'-Z).sub.3-a

where R_f is a polyfluoroalkyl group having from 1 to 20 carbon atoms, X is --R--, --CON(R¹)--Q-- or --SO₂ N(R¹)--Q-- (where R is a divalent alkylene group, R¹ is a hydrogen atom or a lower alkyl group and Q is a divalent organic group), each of A and A'"'"' is --O--, --S-- or --N(Z'"'"')-- (where Z'"'"' is a hydrogen atom or a monovalent organic group), Z is a monovalent organic group, W is a trivalent organic group, a is an integer of 1, 2 or 3. A process for the stainproofing agent is also disclosed.

Claims

1. A stainproofing agent containing as an active ingredient a polyfluoroalkyl-containing compound of the following formula and having a molecular weight of from 800 to 3000:

space="preserve" listing-type="equation">(R.sub.f --X--A--CONH).sub.a --W--(NHCO--A'"'"'--Z).sub.3-a (I)

wherein

R_f is a polyfluoroalkyl group having from 1 to 20 carbon atoms,

X is --R--, --CON(R¹)--Q-- or --SO₂ N(R¹)--Q--, wherein R is alkylene, R¹ is a hydrogen atom or a lower alkyl group and Q is alkylene,

--A'"'"'--Z is selected from the group consisting of ##STR39## --OR'"'"', --OCH₂ CH₂ CN, --OCH₂ CH₂ NO₂, --OCH₂ CH₂ OH, --NHCH₂ OH, --NHCH₂ CH₂ OH, ##STR40## --NHR'"'"', --NR'"'"'R'"'"', --N(CH₂ CH₂ OH)₂ and ##STR41## wherein R'"'"' is an alkyl group, A is --O--, --S-- or --N(Z'"'"')-- wherein Z'"'"' is H or lower alkyl,

W is selected from the group consisting of ##STR42## and a is an integer of 1, 2 or 3.

2. The stainproofing agent according to claim 1, wherein

R_f is a perfluoroalkyl group of the formula C_n F_2n+1 wherein n is 4 to 16,

X is an alkylene of the formula C_m H_2m wherein m is 1 to 10,

A is --O--, and

a is 1 or 2.

3. The stainproofing agent according to claim 1, wherein the polyfluoroalkyl group-containing compound is represented by the formula:

##STR43## wherein R_f, X, A and W are as defined in claim 1,

A¹ is --O--, --S-- or --N(Z'"'"')--,

wherein

Z'"'"' is as defined in claim 1,

Z¹ is a straight chain stearyl group,

A² -Z² is selected from the group consisting of ##STR44## --OR'"'"', --OCH₂ CH₂ CN, --OCH₂ CH₂ NO₂, --OCH₂ CH₂ OH, --NHCH₂ OH, --NHCH₂ CH₂ OH, ##STR45## --NHR'"'"', --NR'"'"'R'"'"', --N(CH₂ CH₂ OH)₂ and ##STR46## wherein R'"'"' is an alkyl group, a is 1 or 2, and

b is 1 or 2.

4. The stainproofing agent according to claim 3, wherein

R_f is a perfluoroalkyl group of the formula C_n F_2n+1 wherein n is 4 to 16,

X is an alkylene of the formula CmH_2m wherein m is 1 to 10,

A is --O--, and

A¹ is --O--.

5. A process for preparing a stainproofing agent, which comprises

reacting a mixture of polyfunctional isocyanate compounds having at least three --NCO groups and a --NHCON<

bond derived from an addition reaction of a >

H--N group-containing compound III with a --NCO group-containing compound IV, wherein the compound III is derived from OCH--Y--NCO, wherein Y is selected from the group consisting of --(CH₂)₆ -- and ##STR47## and the compound IV is OCN--Y--NCO or derived from OCN--Y--NCO where Y is as defined above,

with a compound of the formula R_f --X--A--H wherein

R_f is a polyfluoroalkyl group having from 1 to 20 carbon atoms,

X is --R--, --CON(R¹)--Q-- or --SO₂ N(R¹)--Q--,

wherein R is alkylene, R¹ is a hydrogen atom or a lower alkyl group and Q is a alkylene, and

A is --O--, --S-- or --N(Z'"'"')-- wherein Z'"'"' is a hydrogen atom or a lower alkyl group, and, if required, further reacting the mixture with a compound of the formula Z--A'"'"'--H, wherein A'"'"'--Z is selected from the group consisting of ##STR48## --OR'"'"', --OCH₂ CH₂ CN, --OCH₂ CH₂ NO₂, --OCH₂ CH₂ OH, --NHCH₂ OH, --NHCH₂ CH₂ OH, ##STR49## --NHR'"'"', --NR'"'"'R'"'"', --N(CH₂ CH₂ OH)₂ and ##STR50## where R'"'"' is an alkyl group, to form a mixture of polyfluoroalkyl containing compounds having at least one --NHCO--A--X--R_f group

wherein

A, X and R_f are as defined above,

having a molecular weight of at most 8000 and,

if required, at least one --NHCO--A'"'"'--Z group wherein A'"'"'--Z is as defined above, provided that the total of the --NHCO--A--X--R_f groups and the number of --NHCO--A--Z groups is at least three.

6. The process of claim 7, wherein the mixture of polyfunctional isocyanate compounds is a mixture of polymers obtained by reacting diisocyanate compounds represented by the formula OCN--Y--NCO where Y is as defined in claim 5 with an active hydrogen-containing compound.

7. The process according to claim 5, wherein the mixture of polyfunctional isocyanates comprises from 10 to 90% by weight of a trifunctional isocyanate compound having three --NCO groups and from 10 to 90% by weight of polyfunctional isocyanate compounds having at least four --NCO groups.