TW201100477A - S-perfluoroalkyl substituted hydroxybenzylthioethers and derivatives as surface modifiers - Google Patents

Abstract

The invention describes a composition of comprising an organic material which is susceptible to oxidative, thermal or light-induced degradation, and a compound of the formula I wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is -CH(R11)-S(O)p-R12; R11 is hydrogen, C1-C8alkyl, unsubstituted or with C1-C4alkyl substituted phenyl, R12 is a monovalent linear or branched organic radical containing a perfluorinated alkyl having 6 fully fluorinated carbon atoms, n is 1, 2 or 3, and p is 0, 1 or 2. The invention describes further a process for reducing the surface energy of organic materials such as for example increasing the oil and water repellency and stain release of organic materials, which comprises treating the organic material with at least a compound of the formula I.

Description

201100477 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to an organic material (such as a synthetic polymer) which is susceptible to degradation by oxidation, heat or light, and a transphenylbenzene substituted with an s-perfluoroalkyl group. Methyl 'IL mystery and its composition of the cockroach. The invention is also directed to a method of reducing the surface energy of an organic material comprising treating the organic material with at least one hydroxybenzyl sulfide substituted with 8_perfluoroalkyl and derivatives thereof. [Prior Art] A variety of different fluorochemical compositions are used on fibers or on fibrous substrates such as fabrics, carpets, paper, leather, and nonwoven webs to impart oil repellency and water repellency to, for example, *U Known in s 6,127,485. This reference discloses hydrophobic and oleophobic fibers, films and molded articles comprising synthetic organic polymers in which a fluorochemical compound is dispersed within the fiber, fabric or molded article and present in the fiber, fabric or molded article. On the surface. A suitable S-perfluoroalkyl-substituted hydroxyphenylsulfonyl sulphur for use in a variety of different technical applications, such as for increasing the oil repellency or water repellency of organic materials such as, for example, synthetic polymers, is described in WO 2007/144283. ether. In addition, S-perfluoroalkyl substituted hydroxyphenyl sulfonyl sulfides are also suitable for use in various technical applications, such as the manufacture of modified electret articles. There are a tendency to replace perfluorinated compounds having substituents having 8 perfluorocarbon atoms for a variety of reasons. It has now been found that certain perfluorinated compounds having one or more perfluorinated substituents based only on 6 perfluorocarbon atoms are surprisingly still provided by having 8 or more perfluorocarbons Perfluorinated compounds of atomic substituents 147295.doc 201100477 Known advantageous oil repellency and hydrophobic properties. Although there are no perfluorinated compounds having substituents based on 8 perfluorocarbon atoms, such advantageous water repellency and oil repellency properties can be provided. SUMMARY OF THE INVENTION The present invention relates to a composition comprising: a) an organic material susceptible to degradation by oxidation, heat or light, and b) a compound of formula I

Where η is 1,

Ri is hydrogen, CVC25 alkyl, c2-c25 alkenyl, -0: 〇-115, -(:1^(111())(:〇-r5, -C(R10)2CO-R5, _CO-N( R6)-R7, _CH(R10)CO-N(R6)-R7, -C(R10)2CO-N(R6)-R7, -CHddCOORsi-CdohCO-QRs; 〇 When n is 2, R is not Substituted or via (:1_(^ alkyl, benzyl or phenyl substituted Ci_C24 extended alkyl; C2-C24 extended alkyl via oxygen or sulfur; -CO-R8-CO-, -CH(R10) CO-R8-C〇-CH(R10)- '-C(R10)2CO-R8-CO-C(R10)2-' -CO-N(R6)-R9.N(R6)-CO- ' - CH(R10)CO-N(R6)-R9-N(R6)-CO-CH(R10)- . -C(R10)2CO-N(R6)-R9-N(R6)-CO-C(R10 ) 2- ^ -CH(R10)CO-〇-R9_〇_C〇_CH(Rl0)_ or _c(Ri0)2C〇_〇_R9_〇_ CO-C(Ri〇)2·; When n is 3, 147295.doc -5- 201100477

1 is 0 〇 , R2, R3 and R4 are each independently hydrogen, cvc25 alkyl, c2-C25 thin

H R Η ' —R

OR.

To 4 R or 3 R > 2 R group is attached to a strip but less than -CH^O-SCCOp-Ru; RACi-C: 25 alkyl, CVC25 dilute, unsubstituted or via ^ ^Phenyl or phenyl substituted with phenyl; or C7_Cl2 phenylalkyl, R6 is hydrogen or (VC4 alkyl, R? is hydrogen, Q-C25 alkyl, unsubstituted or via (:1-(:4) Alkyl or halogen substituted phenyl,

Rs is a C1-C24 alkylene group substituted with a phenyl group, unsubstituted or substituted with a fluorenyl group, a benzyl group or a phenyl group; a c2_c24 alkyl group which is intervened by oxygen or sulfur, and R9 is a direct bond, a C2-C24 alkylene group substituted or substituted with a c 1 -c4 alkyl group, a benzyl group or a phenyl group; or a c2_c24 alkyl group interrupted by oxygen or sulfur,

Rio is hydrogen or CVC8 alkyl, R11 is hydrogen, Ci-Cs alkyl, unsubstituted or alkyl substituted phenyl, and R 2 is the unit price of a perfluoroalkyl group having 6 perfluorocarbon atoms. Linear or branched organic group, 147295.doc -6 - 201100477 R13 is hydrogen, Ci-C25 alkyl, C2-C25 alkenyl, -co-r5, -co-n(r6)-R7 or -CH2- C〇-N(R6)-R7,

Rl4 is hydrogen, Ci-C25 alkyl, c2-c25 alkenyl or -CH(Rh)-S(0)p-R12, Ri5 is hydrogen, CVC25 alkyl, C2-C25 alkenyl or -CHdO-SCOVRu, Ri6 Is unsubstituted or via (^-(:4 alkyl substituted methylene, -S-, -S(O)-, -S(0)2- or -c〇_, alkyl, ❹ η 1, 2 or 3, and Ρ is 〇, 1 or 2; but the condition is a compound which does not include hydrazine and hydrazine;

Wherein the composition does not comprise a compound of the formula (I) having a perfluorinated substituent. An alkyl group having up to 25 carbon atoms is a branched or unbranched group such as methyl 'ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, tert-butyl Base, 2-ethylbutyl, n-pentyl, isopentyl, 丨-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3_tetradecylpentyl, fluorenyl, fluorenyl, undecyl, 1-methylundecyl, dodecyl, 11,3,3,5,5-hexamethylenehexyl , thirteen base, fourteen base, fifteen base, sixteen 147295.doc 201100477 base, seventeen base, eighteen base, twenty base or twenty-two base. The alkenyl group having 2 to 25 carbon atoms is a branched or unbranched chain group such as an acryl group, a butyl group, a 3 butyl group, an isobutylene group, a positive 2,4 pentylene group. , 3-methyl-2_butyl group, normal 2_octyl, positive 2-12 complex, isododecenyl, ten-membered, positive 2·ten alkenyl or positive 4—18 Alkenyl. a kb-extension base chain or an unbranched group which is unsubstituted or substituted with a Cl-c4 alkyl group, a benzyl group or a stupid group, such as a methylene group, an ethyl group, a propyl group, a butyl group, and a stretching group.戊基,伸己基,伸庚基,伸辛基伸壬基,伸癸基,伸十基基,伸十二基基,伸十三基伸伸四基基伸十五基,伸六基基,伸七基基, octadecyl, methyl- fluorenylene, ethylmethylene, 2-mercaptopropyl, 2-phenylpropyl, 2-benzylpropionyl, benzylhydrazolyl or phenylpyridinium Base (phenylarylene). The c2-c24 alkyl group via oxygen or sulfur is, for example, _Ch2_〇_CH2_, _Ch2_s-ch2-, _ch2-〇-ch2ch2-, -ch2ch2-o.ch2ch2-, -ch2ch2- 0-CH2CH2- 〇-CH2CH2-, -CH2CH2-(0-CH2CH2-)20_CH2CH2-, -CH2CH2-(〇_CH2CH2-)3〇-CH2CH2-, -CH2CH2-(0-CH2CH2-)4〇-CH2CH2- or -CH2CH2- S-CH2CH2-. A phenyl group substituted with (1:1-alkyl or halogen (which preferably contains 1 to 3, especially 1 or 2 alkyl or halogen groups) is, for example, o-methylphenyl' m-Methylphenyl or p-nonylphenyl, 2,3-didecylphenyl, 2,4-didecylphenyl, 2,5-didecylphenyl, 2,6-di Phenylphenyl, 3,4-didecylphenyl, 3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 4-tert-butylphenyl, 2-ethyl Base, 2,6-diethylphenyl, 2-chlorophenyl, 4-chlorophenyl or 2-hydrazino-4-chlorophenyl. 147295.doc 201100477 Unsubstituted or 1 through phenyl The three CkC4 alkyl substituted <:7-(:12) alkyl group is, for example, benzyl, α-mercaptobenzyl, α,α-didecylbenzyl, 2-phenylethyl, 2- Mercaptobenzyl, 3-decylbenzyl, 4-hydrazinobenzyl, 2,4-dimethylbenzyl, 2,6-dimethylbenzyl or 4-tert-butylbenzyl. Preferably, the monovalent straight or branched chain organic group comprising a perfluoroalkyl group having 6 perfluorocarbon atoms is, for example, _CH2CH2(;CF2;)5CF3. 0 An interesting combination Included is a compound of formula I, wherein 1:00,

Ri is hydrogen, CVC18 alkyl, C2-Ci8 alkenyl, -CO-R5, -co-n(r6)-r7 or -CH2-CO-N(R6)-R7; - when η is 2, R! Substituted unsubstituted or substituted by alkyl, benzyl or phenyl (^-(:) alkyl; by oxygen or sulfur ((2-(:18 alkyl); -CO-Rs-CO·, -CO-N(R6)-R9-N(R6)-CO- or -CH(R10)-CO-N(R6)-R9-N(R6)-CO-〇CH(R10).; when n is 3 o'clock,

R2, R3 and R4 are each independently hydrogen, (VCu alkyl, C2-C18 alkenyl,

-CH(Ri i)-S(0)p-R12 —f >R13 or 147295.doc •9- 201100477 OR., R,

R

Rl4lV1s or13 'but with the condition that the group R2, R3 or R4 is up to 15

One of R17 H is -C^RM-SCO^Ru; R5 is alkyl, C2-Cls alkenyl, unsubstituted or substituted with ^-decyl or halogen; or CrC12 phenylalkyl, R6 Is a chlorine or C1-C4 alkyl group, I is hydrogen, q-Cu alkyl, unsubstituted or via (:1_(:4 alkyl or halogen substituted phenyl, rule 8 is phenyl, unsubstituted or Ci-C24 alkyl group substituted by €1 (:; 4 alkyl, benzyl or phenyl; C2_Cm alkyl group via oxygen or sulfur, h is a direct bond or an unsubstituted (:1_〇4) Alkyl, benzyl or phenyl substituted 02-oxime: 18 alkyl,

Rio is hydrogen or C丨-c8 alkyl,

Rii is hydrogen, CrC:8 alkyl, unsubstituted or alkyl substituted phenyl, R12 is a monovalent straight or branched chain organic group containing a perfluoroalkyl group having 6 perfluorocarbon atoms, R13 is Hydrogen, CVCu alkyl, c2-C18 alkenyl, -C〇-R5, -CO-N(R6)-R7 or -CH2-CO-N(R6)-R7,

Rl4 is hydrogen, Cl_Cl8 alkyl, c2-c18 alkenyl or _CH(R")-S(0)p-R12,

Rl5 is hydrogen, Cl_Cl8 alkyl, c2-c18 dilute or _CH(R")-S(0)p-R12,

Rl6 is an unsubstituted or substituted C1-C4 alkyl group, -S-, _s(o)_, -S(〇)2- or -CO-, 147295.doc •10- 201100477

Rl 7 is a c 1 - C4 alkyl group, n is 1, 2 or 3, and ρ is 0, 1 or 2. A preferred composition comprises a compound of formula 1 wherein Rlz is saturated and contains from 6 to 15 carbon atoms, wherein the six are fully fluorinated and comprise at least one terminal perfluorodecyl group. Also preferred is a composition comprising a compound of the formula wherein ^h Ο and R4 are independently of each other, nitrogen, r r R13〇\ , R14 alkyl,

•R

At least one of H R (1): but with the proviso that the group 15 is -CH(Rii)-S(0)p-R12; R11 is a hydrogen Cl_C8 alkyl group, an unsubstituted or substituted phenyl group via a Ci_c4 alkyl group,

Ru is a monovalent straight-chain or branched-chain organic group containing a perfluoroalkyl group having 6 perfluorocarbon atoms, and ❾Rl3 is chlorine, Cl_Ci8 alkyl, C2-C18-based or ethylenic,

Rl4 is hydrogen, Cl_Cl8 alkyl, C2-C18 dilute or _CH(R")-S(0)p-R12, Rl5 is hydrogen, Cl_Ci8 alkyl, c2-c18 dilute or _CH(R")- S(0)p_R12, R!6 is a methylene group, _s_, _s(〇)_, _8(〇)2_ or _c〇· which is unsubstituted or substituted by Cl_C4 alkyl, and P is 0, 1 Or a composition comprising a compound of formula I, wherein when η is 1, R1 is hydrogen, C"C18 alkyl, -CO-R5, -CO-N(R6)-R7 or- CH2-CO- 147295.d〇c 201100477 Ν(Κ·6)·Κ·7 ; When η is 2,

Ri is unsubstituted or substituted with ^^·^4 alkyl (^-(:8-alkyl); -CO-R8-CO-, -CO-N(R6)_R9-N(R6)-CO- Or -CH(R10)_c〇-N(R6)-R9-N(R6)-CO-CH(Ri〇)-; When η is 3, Ri is

0 0

R R , R 3 and R 4 are each independently hydrogen, Ci-C 8 alkyl

Η or one R

0R13; but it, -CH(Ru)-S (〇V is accompanied by at least one of the groups R2, R3 or r4; the heart is ^-匕8 alkyl, unsubstituted or substituted by hydrazine Phenyl; or C7-C12 phenylalkyl, R6 is hydrogen or CVC4 alkyl, R? is hydrogen, c^-c:8 alkyl, unsubstituted or substituted by (:1_(:4 alkyl) Phenyl, R8 is a phenyl, unsubstituted or gCi_C4 alkyl substituted Ci_Cu alkylene group, 9 is unsubstituted or via (:1_(:4 alkyl substituted alkylene, R10 is hydrogen or alkyl , 11 is hydrogen, CVC8 alkyl, unsubstituted or alkyl substituted phenyl, 2 is saturated and contains 6] 5 carbon atoms, of which 6 carbon atoms are completed 147295.doc -12- 201100477 Fluorine-containing and comprising at least one terminal perfluoromethyl group,

Rl3 is hydrogen, C1-C12 alkyl, -CO-R5, -(:0->1(116)-117 or -(^2-(:0-N(R6).R7,

Rl4 is hydrogen, C1-C12 alkyl or -CH(Rn)-S(0)p-R12,

Rl5 is a Ci-C18 appearance group or _CH(Ru)-S(0)p-R12, and R16 is a methylene group which is unsubstituted or substituted with a fluorene alkyl group, and η is 1, 2 or 3, and 〇 ρ is 0. - a composition of interest comprising a compound of formula I, wherein

Ri2 is -ch2ch2(cf2)5cf3. Of interest is a composition comprising a compound of formula I, wherein when n is 1,

Ri is hydrogen, CVCm alkyl, -C〇-R5, -(:0->1(116)-117 or -(:112-(:0-N(R6)-R7; when η is 2, 〇Rl is C1-C8 alkyl, -CO-R8-CO-, -CO-N(R6)-R9_N(R6)-CO- or -CH(R10)-CO-N(R6)-R9-N (R6)-CO-CH(R10)-; When η is 3,

The heart is 0 0 ,

R2, R3 and R4 are each independently hydrogen, CVC8 alkyl, -CH(Hn)-S(0)p-H or a Rll~^-〇R13; but with the proviso that at least one of the groups r2, R3 or R4 One is -CH(R")-S(0)pR丨2; 147295.doc -13- 201100477 The heart is a phenyl group substituted by an alkyl group, unsubstituted or a heart-and-alkyl group; or a benzyl group , R 7 is hydrogen, CrCs alkyl, unsubstituted or substituted by Crq alkyl, R·8 is phenyl or Ci_Ci8 extended alkyl, Κ·9 is C2-C18 extended alkyl,

Rio is a C1-C4 base,

Rll is hydrogen, C!-C8 alkyl, unsubstituted or via (: 1-(:4 alkyl substituted phenyl),

Ri2 is -CH2CH2(CF2)5CF3, R13 is hydrogen or -c〇-r5, and R14 is hydrogen or CVC8 alkyl.

Ri5 is cvc4 alkyl or _CH(R„)-S(0)p-R12,

Rl6 is a methylene group, η is 1, 2 or 3, and ρ is 0. Also of interest is a composition comprising a compound of formula I, wherein when n is 1,

Rl is hydrogen, Cl_Ci2 alkyl, -CO-R5, -CO-N(R6)-R7 or -CH2-CO-N(R6)-R7; when η is 2,

Rl is an anthracene group, -C〇-R8-CO- or -CH(R10)-CO-N(R6)-R9-N(R6)-CO-CH(R10)-; 147295.doc • 14· 201100477 When η is 3

0

Ri is R2, R3 and R4 are independent of each other as hydrogen «13〇

CVC4 alkyl, -CH(Rn)-S(0)p-

Rl2 or Rl5; but with the proviso that at least one of the groups R2, R3 or R4 is -CH^O-SCCOp-Ru; © R5 is (VC18 alkyl,

Re is gas, h is hydrogen, CrC6 alkyl, unsubstituted or substituted by ^-decyl group,

Rs is a stretching phenyl group, and R·9 is a stretching ethyl group.

Rl 0 is a sulfhydryl group,

Rii is hydrogen, Ci-Cs, phenyl, which is unsubstituted or methyl substituted, R12 is -CH2CH2(CF2)5CF3, R13 is chlorine or ethyl, and ruler 14 is CVC4. R" is -CHdO-SCCOp-Ru,

Ri6 is a methylene group, η is 1, 2 or 3' and ρ is 0 〇 is also of particular interest. The composition of the compound of formula I, 147295.doc -15 · 201100477 When η is 2, R1 is -C Ο - R 8 - C 〇 _, R2, R3 and R4 are independently hydrogen, CVC4 alkyl, -CH(R")-S(0)p- R13°v / 14 -Η,Τ-^Η

Rl2 or 15; but with the proviso that at least one of the groups R2, R3 or R4 is -CHdO-SCCOp-Ru; R8 is a phenylene group, R" is hydrogen, (VC-based, unsubstituted or methylated) Substituted phenyl, R12 is -ch2ch2(cf2)5cf3,

Rl3 is hydrogen or acetyl group,

Rl4 is a C1-C4 yard base.

Ris4 -CH(Rn)-S(0)p-R12 ,

Ri6 is an anthracene group, η is 2, and ρ is 0. Also of particular interest is a composition comprising a compound of formula I, wherein when n is 2,

Ri is -C〇-R8-C〇-;, alkyl or -CHdO-SCOVRu R3 or R4 is at least one of -CH(Rn)-R2, R3 and R_4 are independently of each other; however, the condition is a group &, S(〇)p-R12; 147295.doc -16· 201100477 r8 is a phenyl group,

Rii is hydrogen, CrCs alkyl, unsubstituted or thiol-substituted phenyl, R12 is -CH2CH2(CF2)5CF3, η is 2, and ρ is 0. A composition of particular interest is included as a composition of one of the compounds 101 to 142 of component (b).

F F F F F F

F F F F F F (101)

F F F F F F

(102)

(103)

147295.doc -17- (104) 201100477

(105) (106) (107) (108) 147295.doc -18- (109) (110)201100477 I I I I I F F F F F F ^-s

(Hi)

(CH^C

•C(CH3)3

F F F F F F

F| I I I I I

F F F F F F

F F F F F F

I I I I I |F

F F F F F F (112)

147295.doc

F F F F F F F

(ch3)3c

-19- (113) (114) (115) (116)201100477

H3c 〇-(CH2)„CH3 (118) (Π7)

(119) (120) 147295.doc -20- (121)201100477

F F F F F F

(122)

(123)

VF (124)

(125) 147295.doc -21 (126)201100477

F F F F F F

F F F F F F/-f-l.....1-H-fF < F F F F F F F S

(127)

(128)

(129)

F F F F F F 147295.doc -22 (130) (131)201100477

(132) (133)

F F (134)

F F F F F F

(135) 147295.doc •23· 201100477

ο ο χ U Ο CH3O CHg

(137) F F F F F F F I 1 11 I I F F F F F F (CH3)3C (ch3)3c

F F F F F F F f I I 1 1 1 F F F F F F F (138)

F F F F F F

(139)

Γ F

F F F F F F S-^ F F F F F F Μ M Factory A Η I 1 I 1 f FFFFFF FFFFFF (140) 147295.doc -24- 201100477

(chg3c

(Hi)

(142) Line compounds 104 and 1 〇5 of particular interest. [Embodiment] The compound of the formula I can be prepared by a method similar to that disclosed in U.S. Patent No. 4,874,885, which is incorporated herein by reference. '

Formula. Materials: I compounds are suitable as organic materials which can be used in the composition of the present invention for oil repellency or water repellency. Examples of organic materials are: • Early dilute hydrocarbons and diphenic hydrocarbon polymers, such as polypropylene, polyisobutylene , Poly-polymers..., Polyethylene-based cyclohexenes, polyisoindoles, and ring-based polymers, such as cyclophosphazene or norbornene polymers, polyethylene (its apparent density polyethylene (HDPE) ), high density and ancient: and joint) 'such as South hmw, and A knife quantity polyethylene (HDPE-), 焉 density and ultra-high molecular weight poly-wife (10) PE_UHMW), medium 147295.doc •25· 201100477 density polyethylene ( MDPE), low density polyethylene (LDpE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE). The polyolefin, i.e. the polymer of the monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different and especially by the following methods: a) Free radical polymerization (generally at high pressure and high temperature). b) Catalytic polymerization using a catalyst generally comprising one or more metals of Group lvb, vb, VIb or VIII of the Periodic Table. These metals generally have one or more ligands, which are generally oxides, complexes, alcoholates, esters, ethers, amines, alkyls which are coordinated via τι- or σ-position. , alkenyl and/or aryl. These metal complexes may be in free form or immobilized on a substrate, typically on activated magnesium hydride, titanium (III) chloride, alumina or cerium oxide. These catalysts are soluble or insoluble in the polymerization medium. These catalysts may themselves be used for polymerization or other activators may be used, typically metal alkane, metal hydride, metal alkyl halide, metal alkyl oxide or metal alkyl oxane. Elements of la, Ila and/or llla. These activators are conveniently modified with other ester, ether, amine or mercapto ether groups. Such catalyst systems are commonly referred to as Phillips' Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single active point catalyst (SSC). 2. The polymer mixture mentioned in 1), such as a mixture of polypropylene and polyisobutylene, a mixture of polypropylene and polyethylene (eg PP/HDPE, PP/LDPE) and different types of polyethylene (eg LDPE/HDPE) ) Mix 147295.doc •26- 201100477. 3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, such as ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), polypropylene/ __; μene copolymer, propylene/isobutylene copolymer, ethylene/butyl- ene copolymer, ethylene/hexene copolymer, ethylene/methylpentene copolymer, ethylene/heptene copolymer, ethylene/ Octene copolymer, ethylene/vinyl cyclohexane copolymer, ethylene/cycloolefin co-Q polymer (eg ethylene/norbornene, such as COC), ethylene η-olefin copolymer (where 1-olefin is in situ) Produced); propylene/butadiene copolymer, isobutylene/isoprene copolymer, ethylene/vinylcyclohexene copolymer, ethylene/alkyl acrylate copolymer, ethylene/alkyl methacrylate copolymer, Ethylene/vinyl acetate copolymer or ethylene/acrylic acid copolymer and its salt (ionic polymer) and ethylene and propylene and dilute (such as hexadiene, dicyclopentadiene or ethylidene-norbornene) a polymer; and the copolymers mentioned with each other or with 1) above a mixture of polymers, such as polypropylene/ethylene-propylene co-polymer, LDPE/ethylene-vinyl acetate copolymer (EVA), LDpE/ethylene-acrylic acid copolymer (EAA), LLDPE/EVA, LLDPE/EAA and Alternating or randomly polyalkylene/carbon monoxide copolymers and mixtures thereof with other polymers such as polyamines. 4. According to the tree (for example CyC9), it comprises a hydrogenated upgrade (for example, a tackifier) and a mixture of a polyalkylene group and a starch. The homopolymers and copolymers from 1.) to 4) may have any stereostructure including syndiotactic, isotactic, semi-isotactic or random; wherein a random polymer is preferred. Also included are stereoblock polymers. 147295.doc 27, 201100477 5. Polystyrene, poly(p-nonylstyrene) 'poly(α-mercaptostyrene). 6. Aromatic homopolymers and copolymers derived from ethylene-based aromatic monomers, including styrene, α-mercaptostyrene, vinyl toluene (especially for ethylene-terphenyl) The structure, all isomers of ethyl styrene, propyl styrene, vinyl biphenyl, vinyl naphthalene and vinyl anthracene and mixtures thereof. The homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, semi-isotactic or random; wherein a random polymer is preferred. Also included are stereoblock polymers. a 6a-copolymer comprising the aforementioned vinyl aromatic monomer and selected from the group consisting of acetylene, propylene, diene, nitrile, acid, maleic anhydride, maleimide, vinyl acetate, and ethylene or acrylic acid derived And comonomers of mixtures thereof, such as styrene/butadiene, styrene/acrylonitrile, styrene/ethylene (interpolymer), styrene/alkyl methacrylate, styrene/butadiene/ Alkyl acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride, styrene/acrylonitrile/decyl acrylate; high impact strength styrene copolymer and another polymer a mixture, such as a polyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer; and a block copolymer of styrene, such as styrene/butadiene/styrene, styrene/isoprene Alkene/styrene, styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene. Hydrogenated aromatic polymers derived from the hydrogenation of φζ and its polymers, especially polycyclohexylethylene (PCHE) made from hydrogenated atactic polystyrene, commonly referred to as polyvinylcyclohexane ( PVCH). 6c. Hydrogenated aromatic polymerization derived from the hydrogenation of polymers mentioned in 6a.) 147295.doc •28· 201100477. The homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, semi-isotactic or random; wherein a random polymer is preferred. Also included are stereoblock polymers. 7. A graft copolymer of a vinyl aromatic monomer (such as stupid ethylene or methyl styrene) such as styrene grafted onto polybutadiene and styrene grafted to polybutadiene-benzene Ethylene or polybutadiene-acrylonitrile copolymer; styrene and hydrazine acrylonitrile (or methacrylonitrile) grafted on Ding Erfu; styrene, propylene and methacrylic acid Branched on Polybutyx; phenylethyl and maleic acid liver grafted onto polybutadiene; styrene, propylene guessed maleic acid needle or maleimide grafted onto polybutadiene Styrene and maleimide are grafted onto polybutadiene; styrene and alkyl acrylate or alkyl methacrylate are grafted onto polybutadiene; styrene and acrylonitrile grafted On ethylene/propylene/diene terpolymer; styrene and acrylonitrile grafted onto polyalkyl acrylate or polyalkyl methacrylate, styrene and acrylonitrile grafted onto acrylate/butadiene A mixture of a dilute copolymer and its copolymers as listed in 6), for example a copolymer mixture known as ABS, MBS, ASA or AES polymer. 8. Halogen-containing polymers such as gas butyl dichloride, chlorinated rubber, isobutylene-isoprene gasification and brominated copolymers (halogen butyl rubber), chlorinated or sulphur chlorinated polyethylene, ethylene and a copolymer of ethylene chloride, a gas alcohol homopolymer and a copolymer, especially a polymer of a vinyl compound containing a hydroxyl group, such as polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride And copolymers thereof such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate copolymer. 147295.doc •29- 201100477 9. Polymers derived from α,β-unsaturated acids and their derivatives, such as polyacrylic acid vinegar and polymethyl acrylate vinegar, polymethyl methacrylate vinegar, poly Acrylamide and polyacrylonitrile, impact modified by butyl acrylate. 10· 9) The copolymers mentioned in the monomers or with other unsaturated monomers, such as acrylonitrile/butadiene copolymer, acrylonitrile/alkyl acrylate, propylene guess Diluted acid aerobics base or propylene guess / haloethylene copolymer or acrylonitrile / alkyl methacrylate / butadiene terpolymer. 11. Polymers or mercapto derivatives derived from unsaturated alcohols and amines or their condensation systems, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl polystearate, polyethylene benzoate, polymaleic acid Ethylene, polyvinyl butyl hydride, polypropyl propyl phthalate or polypropyl melamine; and copolymers thereof with the above-mentioned 1). 12. Homopolymers and copolymers of cyclic ethers, such as polyalkyl diols, polyethylene oxides, polyglycidyl or copolymers thereof with bisglycidyl ethers. 13. Polyacetals, such as polyoxymethylene and their polyoxyfurfural containing oxyethylene acetonide as a comonomer; polyacetal modified with thermoplastic polyamino phthalate, acrylate or MBS. 14. Polystyrene and polystyrene and mixtures of polyphenylene ether with styrene polymers or polyamines. 15. An aspect from a hydroxyl terminated polyether, polyester or polybutadiene and, on the other hand, a polyurethane derived from an aliphatic or aromatic polyisocyanate and a precursor thereof. 16. Polyamines and copolyamines derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or corresponding internal amines, such as polyamine 4, polyamine 6, polyamine 147295. doc • 30- 201100477 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamido n, polyamido 12, starting with m-xylylenediamine and adipic acid Aromatic polyamine; a polyamine prepared from hexamethylenediamine and isophthalic acid or/and terephthalic acid with or without an elastomer as a modifier, such as poly-2,4,4- Trimethyl hexamethylene phthalic acid or poly-m-phenyl-phenyl dimethyl hydrazine; and the aforementioned polyamine and polyolefin, olefin copolymer, ionic polymer or chemically bonded or grafted a block copolymer of an elastomer, or a block copolymer with a polyether (for example, polyethylene glycol, polypropylene glycol or polytetramethylene glycol); and a polycondensate modified by EPDM or ABS Amine or copolyamine; and polyamine (RI1V [polyamine system) condensed during processing. 17. Polyurea, polyimine, polyamine, phthalimide, polyether phthalimide, polyacetamide, polyethyl carbazide and poly benzoic acid. sit. 18_ from dicarboxylic acid And diols and/or polyesters derived from hydroxycarboxylic acids or corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-hydroxyindole ring Alkyl terephthalate, polyalkylene naphthalate bismuth (PAN) and polyhydroxybenzoate, and block copolyetherester derived from hydroxyl terminated polyether; and polycarbonate Or MBS modified polyester. 19. Polycarbonate and polyester carbonate. 20·Julu, polyether oxime and polyether. 21. Aspects derived from aldehyde and on the other hand derived from phenol, urea and melamine Cross-linked polymers such as phenol/furfural resins, urea/formaldehyde resins and melamine/furfural resins. 22. Dry and non-drying alkyd resins 23. Copolyesters of self-saturated and unsaturated dicaptanic acid and polyols And the unsaturated polyester resin derived from the vinyl compound derived from 147295.doc * 31 - 201100477 and its low flammability halogen-containing modified substance. Acrylate-derived crosslinkable acrylic resin, such as epoxy acrylate, amine phthalate acrylate or polyester acrylate. 25. melamine resin, urea resin, isocyanate, trimeric isocyanate, polyisocyanate or epoxy Resin-crosslinked alkyd resin, polyester resin and acrylate resin 26. Crosslinked epoxy resin derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, such as bisphenol A and bisphenol A product of F diglycidyl ether, crosslinked with a conventional hardener such as an anhydride or an amine, with or without an accelerator. 27. Natural polymers such as cellulose, rubber, gelatin and their chemical modifications Homologous derivatives, such as cellulose acetate, cellulose propionate and cellulose butyrate or cellulose ether (such as decyl cellulose); and rosin and its derivatives. 28. Blend of the aforementioned polymers (Polyblend), such as PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/ CPE, PVC/Acrylate, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymer, PA/HDPE 'PA/PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC. Forming and synthesizing organic materials, which are pure monomeric compounds or mixtures of such compounds, such as mineral oils, animal and vegetable fats, oils, and 147295.doc -32-201100477, or based on synthetic vinegar (phthalic acid vinegar, Adipic acid vinegar, citric acid s or phthalate ester oils, fats and waxes, and any combination of weight ratios and mineral oils, etc., such as spinning compositions Μ = waterborne Emulsion. ~ etc. = or an aqueous emulsion of synthetic rubber, such as a natural latex or a thiol-based ethylene/butyl-dilute copolymer of milk.最好 Preferred organic materials are natural, semi-synthetic or (preferably) synthetic polymers. The σ Tejia organic material is a synthetic polymer, and the most preferred is a thermoplastic polymer. Particularly preferred organic materials are polyacetals, polyolefins (such as polypropylene or polyfluorene/polyurethane vinegar, polyester (such as poly(p-butylene dicarboxylate) or polyamidamine. The performance of the compound as a surface energy reducing agent for organic materials. The right organic material with low surface energy has properties such as, for example, water repellency and oil repellency, hydrophobicity, barrier susceptibility, self-cleaning, Easily decontaminating agent or solvent resistance. Preferably, the compound of formula 1 is added in a concentration of from 1 to 10%, preferably from 0.01 to 2% by weight of the material, generally 〇1 main 2 /〇. The invention is also in the form of a composition in the form of a masterbatch or a concentrate, i comprising from 5 to 90% by weight of the eight-eighth, and the knife (a) and the weight of 5 to 80 % of the component (b) excluding the formula 々k. In addition, the composition of the invention may include other additives such as, for example, the following: 1. Antioxidant 147295.doc • 33· 201100477 1.1• Alkalized singles such as 2,6-di-t-butyl-4-methyl, 2-tert-butyl-4,6-di Phenol, 2,6-di-t-butyl-4-tetraethylphenol, 2,6-di-t-butyl-4-n-butylphenol, 2,6-di-t-butyl- 4_ Butylphenol, 2,6-dicyclopentyl-4-nonylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-bisoctadecyl_4_ Methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethoxyphenol, nonylphenol which is a direct bond or a branched chain in the side chain, For example, 2,6-di-mercapto-4-nonylphenol, 2,4-dimercaptodecyl eleven-1'-yl)phenol, 2,4-dimercapto-6-(1,-methyl 17,1,1,ylphenol, 2,4-dimercaptodecyltridecylidene-ylphenol and mixtures thereof. 1.2. Sodium thiomethylphenol, such as 2,4_dioctylthioguanyl-6_t-butylphenol, 2,4-dioctylthiononyl-6-nonylphenol, 2,4_ Dioctylthioguanyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol. 1.3. Hydrogenation and alkylation of hydroquinone, such as 2,6-di-t-butyl-4-yloxy, 2,5-di-second butyl hydrogen, 2,5-di- Tri-amylhydroquinone, 2,6-diphenyl-4-enostearyl phenol, 2,6-di-t-butyl fluorene, 2,5-di-t-butyl-4- Hydroxyphenyl ether, 3,5-di-t-butyl-4-hydroxybenzoate, 3,5-di-t-butyl-4-hydroxyphenyl stearate, double, 5_di- Third butyl-4-phenylphenyl) adipate. 1. 4·Tocopherols such as α-tocopherol, β-tocopherol, 7-tocopherol, §_tocopherol and mixtures thereof (vitamin oxime). 1.5·hydroxylated thiodiphenyl ether, such as 22 ι_ thiobis (6-t-butyl-4-indolyl), 2,2'-thiobis(4-octyl), 4,4,- Thiobis(6-tert-butyl-3-nonylphenol), 4,4'-thiobis(6-tert-butyl-2-nonylphenol), 4,4,-sulfur double (3,6 -di-second amyl phenol), 4,4'-bis(2,6-diamidino-4-hydroxyphenyl) disulfide. 147295.doc •34- 201100477 1·6·alkylene bisphenols, such as 2,2′-methylenebis(6-t-butylmethylphenol), 2,2·-methylene double (6- Tributyl-4-ethyl base), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2,-methylene double (4 -methyl_6·cyclohexylphenol), 2,2,-methylenebis(6-fluorenyl-4-methylphenol), 2,2'·indolyl bis (4,6-di- Tributylphenol), 2,2,-ethylenebis(4,6-di-t-butylphenol), 2,2'-ethylenebis(6-tert-butyl-4-isobutyl) Phenol), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6_(α,α-dimethyl Benzyl)-4-nonylphenol], 4,4,-methylenebis(2,6-di-t-butylphenol), 〇4,4'-methylene double (6-third Butyl-2-nonylphenol), 1,1-bis(5-t-butyl-4-fluorenyl-2-methylphenyl)butane, 2,6-bis(3-tert-butyl巧-mercapto-2-ylbenzyl)-4-nonylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-indolyl)butane, 1, 1-bis(5-t-butyl-4-hydroxy-2-indolyl-phenyl)-3-n-dodecyldecylbutane, ethylene glycol bis[3,3-double 3'-Tertibutyl-4·-hydroxyphenyl)butyrate], bis(3-t-butyl-4-hydroxy-5-mercapto-phenyl)dicyclopentadiene, bis[2 -(3^Telebutyl-21-hydroxy-5'-mercaptobenzyl)-6-tert-butyl-indenyl 4-indenylphenyl]terephthalate, 1,1-di- (3,5-Dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-dual (5 -T-butyl-4-hydroxy 2-indolylphenyl)-4-n-dodecyldecylbutane, 1,1,5,5-tetra-(5-t-butyl-4-hydroxy- 2-nonylphenyl)pentane. ·., Ν-, Ν- and S-benzyl compounds, such as 3,5,3,,5,-tetra-tert-butyl-4,4'-di- benzyl ether, octadecyl _4_经基_3,5-Dimethylbenzyl decyl acetate, tridecyl-4-hydroxy-3,5-di-t-butylbenzyl sulfhydryl B SslSb, two (3,5_ Di-di-dibutyl _4_ cis-yl) amine, bis(4_t-butyl-3-yl-2,6-monomethyl-V) disulfide terephthalate (3,5-II_147295.doc •35- 201100477 Third butyl-4-hydroxybenzyl) sulfide, isooctyl_3,5-di-t-butyl _4_ hydroxybenzyl decyl Acid ester. 1.8. Benzylated malonic acid vinegar, such as bis-octadecyl-2,2-bis(35--t-butyl-2-n-phenylbenzyl)malonate, di-octadecyl-_2 (3_r: butyl-4-hydroxy-5-mercaptobenzyl)malonate, di-dodecylmercaptoethyl 2,2_bis(3,5-di-t-butyl- 4-Phenylbenzyl)malonate, bis['(丨, 〗 3 % tetramethylbutyl) benzyl]-2,2-bis(3,5-di-t-butyl- 4- Via basal base) malonic acid vinegar. 1.9. Aromatic hydroxybenzyl compound, for example, succinyldi-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di -Tertiary butyl 4-hydroxybenzyl)·2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-trans-base Base) hope. 1.10. Triazine compounds, such as 2,4-bis(octylfluorenyl)-6-(3,5-di-t-butyl-4-hydroxyanilino)-l,3,5-triple, 2- Octylthio-4,6-bis(3,5-mono-t-butyl-4-phenylanilino)-1,3,5-tripa, 2-octyl-based _4,6-bis ( 3,5-di-t-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-t-butyl-4-hydroxyl Phenoxy)-indole, 2,3-triazine, iota, 3,5-tris(3,5-mono-dibutyl-4-butylbenzyl)isocyanuric acid g, 1, 3,5-tris(4 _ second butyl-3-transyl-2,6-dimethylbenzyl)isomeric cyanurate, 2,4,6-tris(3,5-- - Dibutyl-4-phenylphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-t-butyl-4-hydroxyphenylpropanyl Hexahydro-H5-tripa, 1,3,5-bis(3,5-dicyclohexyl-4-hydroxyl)polycyanate. 1. Π·benzylphosphonate, such as dimethyl 2-,5-di-t-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-t-butyl-4-hydroxybenzylphosphonic acid 147295.doc -36- 201100477 酉曰bis-octadecyl 3,5-di-t-butyl-4-hydroxybenzylphosphonate, bis-octadecyl-5-t-butyl _4_ _3_Methyl sulphate, a calcium salt of a monoethyl ester of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid. 1.12·Alkylamine group Alkaloids, quaternary stearylamine, octyl N-(3,5-di-t-butyl-4-hydroxyphenyl)amino phthalate. ·13·β_(3 , 5---t-butyl-4-hydroxyphenyl)propionic acid with single or multiple

Alcoholic vinegar, for example, with oxime, ethanol, n-octanol, isooctanol, stearyl alcohol, 1,6-hexanediol, anthraquinonediol, ethylene glycol, hydrazine propylene glycol, neopentyl glycol, Sulphur diethylene glycol, diethylene glycol, triethylene glycol, neopentyl alcohol, tris(hydroxyethyl) iso-cyanuric acid vinegar, team price _ bis (hydroxyethyl) oxalylamine, 3 sulphur Decadol, 3-thiopentadecanol, dimethylhexanediol, trihydroxydecylpropane, 4-carbylmethyl-hydrazine-filled-2,6,7-trioxabicyclo[2 2 2] Octane. T.14. β-(5-Tertiary-4-hydroxy-3-yl-nonylphenyl)propionic acid and mono- or polyhydric alcohol ||_, for example with methanol, ethanol, n-octanol, isooctanol , stearyl alcohol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, hydrazine, 2-propane diol, neopentyl glycol, thiodiglycol, diethylene glycol, three Glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, hydrazine, Ν'-bis(hydroxyethyl) oxaloin, 3- thioundecyl alcohol, 3-thiopentadecanol, Trimethyl hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phosphono-2,6,7-trioxabicyclo[2·2 2]octane; 3,9-double [2 -{3_(3_Tertibutyl-4-hydroxy-5-methylphenyl)propoxyphene 1,1-dimethylethyl]_2,4,8,10·tetraoxaspiro[ 55] Undecane gas. 1·15· An ester of Ρ-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with a mono- or polyhydric alcohol, for example with methanol, ethanol, octanol, octadecyl alcohol, hydrazine, 6-hexane Alcohol, 147295.doc •37· 201100477 1,9-decanediol, ethylene glycol, 12-propanediol, neopentyl glycol 'thiodiethylene glycol, diethylene glycol 'triethylene glycol, neopentyl alcohol , tris(hydroxyethyl)isocyanate, N,N'-bis(hydroxyethyl)oxalylamine, % thioundecyl alcohol, 3- thiopentadecanol, dimethyl hexanediol , a complex of trishydroxypropyl propyl, 4-hydroxydecyl-1-linhe-2,6,7-trioxabicyclo[2 2 2]octane. 1·16·3, an ester of S-di-t-butyl-4-ylhydroxyphenylacetic acid with a mono- or polyhydric alcohol', for example with decyl alcohol, ethanol, octanol, stearyl alcohol, 16-hexanediol, 1 , 9_decanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol monoethyl alcohol, diethylene glycol 'neopentitol, tris(hydroxyethyl) iso Polycyanate, N, N'-bis(hydroxyethyl) oxazamide, 3-thioundecyl alcohol, 3-thiopentadecanol, dimercaptohexanediol, trihydroxydecylpropane, 4 _Hydroxymercaptophosphono-2,6,7-trioxabicyclo[2·22]octane. I.17. Indoleamine of Ρ-(3,5·di-t-butyl-4-ylhydroxyphenyl)propanoic acid, such as hydrazine, Ν'·bis(3,5-di-t-butyl- 4 _Hydroxyphenylpropanyl)hexamethylenediamine, hydrazine, Ν'·bis(3,5-di-t-butyl-4-hydroxyphenylpropanyl)trimethylenediamine, Ν,Ν,-bis(3,5-di-t-butyl-4-hydroxyphenylpropanyl), Ν,Ν,Ν'-double [2-(3-[3,5-di- Tributyl-4-hydroxyphenyl]propenyloxy)ethyl]campamine (Naugard® XL-1 supplied by Uniroyal). 1.18. Ascorbic acid (vitamin c) 1.19. Amine antioxidants such as n,N,-di-isopropyl-p-phenylene diamine, hydrazine, Ν'-di-second butyl pair Phenyldiamine, n,N'-bis(1,4-didecylpentyl)-p-phenylenediamine, N,N,-bis(1-ethyl-3-decylpentyl ) _ p-phenylenediamine, N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N,-dicyclohexyl-p-phenylene diamine, N,N,-diphenyl-p-phenylene diamine, 147295.doc -38- 201100477 N,N'-bis(2-naphthyl)-p-phenylene diamine, N-isopropyl -Ν'-phenyl-p-phenylenediamine, N-(l,3-dimethylbutyl)-oxime-phenyl-p-phenylenediamine, N-(l-methylglycol ))-Ν'-phenyl-p-phenylene diamine, Ν-cyclohexyl-Ν'-phenyl-p-phenylene diamine, 4-(p-toluidinesulfonyl)diphenyl Amine, hydrazine, Ν'-dimercapto-fluorene, Ν'-di-t-butyl-p-phenylene diamine, diphenylamine, decylallyldiphenylamine, 4-isopropyl Oxydiphenylamine, fluorenyl-phenyl-1-naphthylamine, fluorenyl-(4-indenyl-octylphenyl)-1-nylamine, fluorenyl-phenyl-2-nylamine, octyl Diphenyl For example, ρ,ρ'-di-t-octyldiphenylamine, 4-n-butylaminophenol, 4-butenylaminophenol, 4-mercaptoaminophenol, 4-dodecylamine Phenol, 4-octadecylaminophenol, bis(4-methoxyphenyl)amine, 2,6-di-t-butyl-4-dimethylaminononylphenol, 2,4 '-Diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, hydrazine, hydrazine, hydrazine, Ν'-tetramethyl-4,4'-diaminodiphenyl decane 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(Γ,3 '_Dimethylbutyl)phenyl]amine, trioctylphosphonium-phenyl-1-naphthylamine, a mixture of mono- and dialkylated tert-butyl/t-octyldiphenylamine , a mixture of mono- and dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines , a mixture of mono- and dialkylated tert-butyldiphenylamine, 2,3-dihydro-3,3-dimercapto-4Η-1,4-benzothiazine, phenothiazine, mono- and a mixture of dialkylated tert-butyl/tris-octylphenothiazine , a mixture of mono- and dialkylated tert-octyl-phenothiazine, fluorenyl-allylphenothiazine, anthracene, fluorene, Ν', Ν'-tetraphenyl-1,4-diaminobutyl - 2- argued r. 2· UV absorber and light stabilizer 147295.doc -39- 201100477

2-(5'-tert-butyl-2 triazole, 2-(2i-hydroxy-5'-(1,1,3,3-tetramethyl-butyrate, floc|, 岔--,. _ _

&open diazole, such as 2-(2,-hydroxy-5.-methyl 5'-di-t-butyl 2,-hydroxyphenyl)benzo-p-phenyl)benzotriazole, 2_(2,_鞞(3',5'_bis-(α,α-dimethylbenzyl wm ^•甘,# 2 .

Third butyl, hydroxybenzoquinone-based Ikylethyl)phenyl)-5-chloro-benzotrienyl, 2_(3'_t-butylidene 2, hydroxy-5'-(2-曱oxycarbonylethyl)phenyl)benzotriazole, 2_(3,_t-butyl-2'-hydroxy-5'-(2-octyloxycarbonyl)phenyl)benzotriazole , 2_(3,_ 2,4-butyl-5 _[2-(2-ethylhexyloxy)|1 carbonylethyl]_2'-pyridylphenyl)benzotrisole, 2-(3' -dodecyl-2'-trans-yl-S'-methylphenyl) phenylindole, 2·(3·-tert-butyl-2'-hydroxy-5'-(2-isooctyloxy) Carbocarbonylethyl)phenylbenzotriazole, 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)_6_benzotriazin-2-ylphenol 2-[3·-T-butyl-5·-(2-methoxycarbonylethyl)·2,-yl-phenylidene]-2Η-benzobis-pyrene and polyethylene glycol 3 00 Cooling product; [R-CH2CH2-C00-CH2CH2k, where R=3,-t-butyl-4,-hydroxy_5ι_2Η_benzotrix-2-ylphenyl, 2-[2'- Mercapto-3·-(α,α-dimethylbenzyl) (1,1,3,3-tetradecylbutyl)-phenyl]benzotrisyl; 2-[2,-trans-base- 3'- 147295.doc -40- 201100477 (1,1,3,3-tetramethylbutyl -5'-(α,α-dimercaptobenzylidyl) sloppy and three-seat sitting 2.2. 2-hydroxybenzophenone, such as 4-hydroxyl, 4-decyloxy, 4-octyloxy, 4-decyloxy, 4-undecyloxy, 4-hydroxy, 4,2',4'-tri- and 2-hydroxy- 4,4'-dimethoxy derivatives. · 3 · Substituted and unsubstituted benzoic acid esters, such as 4 tert-butyl phenyl phenyl salicylate, phenyl salicylate, octyl phenyl salicylate, diphthyl benzoate Resorcinol, bis(4-t-butylphenyl fluorenyl) m-bromophenol, phenylhydrazino resorcinol, 2,4-di-t-butylphenyl 3,5_2 _Tertiary butyl 4-hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, octadecyl 3,5-di-t-butyl _ 4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-t-butyl-4-hydroxybenzoate. 2.4. Acrylate, such as B Base 〇 1-cyano _13, didiphenyl acrylate, isooctyl α-cyano-β, β-diphenyl acrylate, methyl α-methoxymethyl cinnamate, methyl α -Cyano (3_methyl-p-methoxy cinnamate, butyl α_ 氰 cyano Base-p-oxime-cinnamate, methyl (X-decyloxymercapto-p-methoxycinnamate, Ν-(β-methoxycarbonylcyanovinyl)_2_曱Basil porphyrin, neopentyl tetra(α-cyano-β, β-diphenyl acrylate. 2.5. Record a nickel complex of the compound 'for example 2,2,-sulfo-bis[4_(11,3,3-tetramethylbutyl)phenol], such as with or without additional ligands such as n-butyl 1:1 or 1:2 complex of amine, diethanolamine or Ν-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, 4•hydroxy-3,5-di-tert-butylphosphinylphosphine a nickel salt of a monoalkyl ester of an acid (eg, a f- or ethyl ester), a nickel complex of a ketoxime (eg, 2-hydroxy-4-methylphenylundecyl oxime), with or without additional Bit 147295.doc -41- 201100477 The nickel complex of 1-phenyl·4·monthlyl I via group (IV). 2·6·sterically hindered amines such as bis (2 2,6 6_tetradecyl) such as phthalate, bis (2,2,6,6-tetramethyl 4 r... Base-4-piperidyl) succinate, bis(1,2,2'6,6-pentamethyl-4-bryridinyl) sebacate, bis(1-octyloxy-2.2. 6.6-tetramethyl as a base bite) sebacic acid _, bis (1,2,2,6,6-pentamethyl-yl)-n-butyl-3,5_di-tert-butyl_4_ The benzylidene methyl hydroxy hydroxyacetate, 1-(2-ethyl)-2,2,6,6-tetramethyl-containing methyl hydrazine-methyl-4-hydroxypiperidone. a condensate of hydrazine with a sulphonic acid, N,N'-bis(2,2,6,6-tetramethyl,j 6 w,f-yl-4-piperidyl)hexamethylenediamine and 4_ second a linear or cyclic condensate of octylamino-2,6-dioxazol 2 2 c* 13,5-diazine, bis(2,2,6,6-tetramethyl-4) It is a strip and a 7-negative & soil) enthalpy, 肆 (2, 2, 6, 6 - tetradecyl-4-group) _ι 2 3 4 -r~ u } , , 4-butane tetradecanoate, 1,1,-(1,2-ethanediyl)_bis (3,3,5,5-tetradecyl.皋_ Nai), 4-phenyl Mercapto-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2 2 ,6,6-tetradecylpiperidine, bis (1,2,2,6,6 -pentamethylpiperidinyl)-2-n-butyl-2-(2#* Λ. ^ z (2'hydroxy-3,5-di-t-butylbenzyl)malonate, 3-positive Octyl _7 7 9 q bauxite, tetramethyl-1,3,8-triazaspiro[4.5]decane- 2,4-di-, bis (i-octyloxy, 2,6, 6-tetradecyl η Chen bite base) azelaic acid vinegar, bis(1-octyloxy-2,2,6,6-tetrada# ^ w methylpiperidinyl) succinate, hydrazine, Ν' -Bis(2,2,6,6-tetramethyl_4_^σ, 丄疋I) hexamethylenediamine and 4-morpholinyl-2,6-dichloro-1 , 3,5-trisole linear or condensate, 2_chloro-4,6_bis(4_n-butylamino-2,2,6,6-tetramethylpipera I-crossing Condensation of -H5-triazine with i,2-bis(3-aminopropylamino)ethyl 舲% oxime, 2-chloro-4,6-di-(4-n-butylamino)- 1.2.2.6.6- pentamethyl bristo, and & volume) '1,3,5-triazine and 1,2-bis(3-aminopropylamino) ethane condensate, 8 7 1*= &Hexyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro-[5]癸J Liukeng-2,4- Diketone, 3-dodecyl- l-(2,2,6,6-147295.doc •42- 201100477 tetradecyl-4-piperidinyl)pyrrolidine-2,5-dione, 3-ten Dikilad-1-(1,2,2,6,6-pentamethylene-4-pyranyl)pyrrolidine-2,5-dione, 4-hexadecyloxy- and 4-stearin Mixture of oxy-2,2,6,6-tetramethylnipine, N,N'-bis(2,2,6,6·tetradecyl-4-piperidyl)hexamethylenediamine Condensate with 4_cyclohexylamino 2,6-dichloro- 3,5-triazine, 1,2-bis(3-aminopropylamino)ethane and 2,4,6- Dihydrate-1,3,5-diindole and 4-butylamino-2,2,6,6-tetradecyl brigade condensate (CAS Reg. No. [136504-96-6]); 1,6-hex Diamine and 2,4,6·0 trichloro-1,3,5-triazine and hydrazine, hydrazine-dibutylamine and 4-butylamino-2,2,6,6-tetradecylperidine A condensate of pyridine (CASReg. No. [192268-64-7]); N-(2,2,6,6-tetradecyl-4-latyridyl)-n-dodecyl amber quinone imine, N -(1,2,2,6,6-pentamethyl_4_biti)-n-dodecyl amber imine, 2-undecyl-7,7,9,9-tetramethyl 1_oxa-3,8-diaza-4-yloxy-spiro[4,5] brothel, 7,7,9,9-tetramethyl-2-cyclo[yl]-1-oxa -3,8-diaza-4-oxooxa-[4,5]decane and epichlorohydrin reaction product, pentamethyl-4-piperidinyloxycarbonyl)-2-(4-methyl Oxyphenyl)ethylene, ν,Ν'-bis-indole-indole, anthracene-bis(2,2,6,6-tetradecyl-4-brenyl)hexamethylenediamine, 4 - a mixture of decyloxymethylenemalonic acid and 1,2,2,6,6-pentamethyl- 4-hydroxypiperidine, poly[mercaptopropyl-3-oxo-4-(2, 2,6,6-tetradecyl-4-piperidinyl)]nonane, maleic anhydride-α-olefin copolymer and 2,2,6,6-tetradecyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine reaction product, 2,4-bis[N-(l-cyclohexyloxy-2,2,6,6-tetramethyl) Isopiperidin-4-yl)-indole-butylamino]-6-(2-hydroxyethyl Amino-1,3,5-diindole, 1-(2-lightyl-2-methylpropoxy)-4-octadecyloxy-2,2,6,6-tetramethylper Pyridine, 5-(2-ethylhexyl)oxymethyl-3,3,5-trimethyl-2-oxanone, Sanduvor (Clariant; CAS Reg. No. 147295.doc -43- 201100477 106917 -31-1]), 5-(2-ethylhexyl)oxyindol-3,3,5-trimercapto-2-morpholinone, 2,4-bis[(1-cyclohexyloxy) Base 2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-S.triazine with N,N,-bis(3-aminopropyl)-extended ethyl Reaction product of amine, 1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazine-3-fen-4-yl)amino)-3- Triazine, 1,3,5-tris(>1-cyclohexyl-:^-(1,2,2,6,6-pentamethylpiperazin-3-one-4-yl)amino)- S-triazine. 2.7. Grassy amines such as 4,4'-dioctyloxyxanthenil, 2,2,-diethoxysalbenzilide, 2,2'-dioctyloxy-5,5'- Di-t-butyl oxalic acid aniline, 2,2'-docosyloxy-5,5'-di-t-butyl oxalicone, 2-ethoxy-2'-ethyl Physicide, NW-bis(3-dimethylaminopropyl) oxazamide, 2-ethoxy-5-tert-butyl-2^ethylglyoxime and its 2- and B a mixture of oxy-2'-ethyl-5,4'-di-t-butylglyoxime, a mixture of o- and p-methoxy disubstituted oxalic anilides A mixture of p-ethoxy substituted diphenyl anilide. 2.8. 2-(2-Phenylphenyl)-1,3,5-triterpene', for example 2,4,6-tris(2-yl-4-octyloxyphenyl)-1,3,5 -Triterpenoid, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-i,3,5-triazine, 2-(2 ,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-i,3,5-triazine, 2,4-bis(2-hydroxy-4-propoxy Phenyl)-6-(2,4-dimethylphenyl)dj,% triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylbenzene Base; μ 13,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimercaptophenyl)_1,3,5_ Triazine, 2_(2-hydroxy-4-indolyloxyphenyl)-4,6-bis(2,4-dimercaptophenyl)-indole, 3,5-triazine, 2-[2- Hydroxy-4-(2-hydroxy-3-butoxypropoxy)phenyl]_4,6 bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxyl _4_(2_hydroxy_3_octyloxypropoxy)benzene 147295.doc -44 - 201100477 base]-4,6-bis(2,4-dimercapto)_i,3,5-triazine, 2_[4_(dodecyloxy/dodecyloxy-2-pyridyloxy)_2-hydroxyphenyl]_4,6-bis(2,4-dimethylphenyl)-1,3 , 5-diazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxy) Oxy)phenyl]-4,6-bis(2,4-dimethylphenyl)triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyltriazine , 2-(2-hydroxy-4-yloxyphenyl)-4,6-diphenyl 4,3,5-triazine, 2,4,6_tri[2-hydroxyl-4 (3 butoxide) 2-hydroxypropoxy)phenyltriazine, 2-(2-hydroxyphenyl)-4_0 (4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2- {2-Hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropoxy]phenyl}_4,6-bis(2,4-dimethylphenyl)- 1,3,5-triazine, 2,4-bis(heart [2-ethylhexyloxy]-2-hydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-three 3. Metal passivator, for example, n, N'-diphenyl oxazamide, N-water phlegm _n, - water 醯 醯 肼, Ν, Ν, - double (水扬醯) 肼, ν,Ν,-bis(3,5-di-t-butyl-4-phenylphenylpropyl fluorenyl) fluorene, 3-hydralylamino-1,2,4-triazole, bis ( Phenylene) oxadiazepine, oxalic anilide, m-xylylene hydrazide, fluorenyl bisphenyl fluorene, N,N,-diethyl decyl hexamethylene二醯肼,Ν,Ν·-双(水扬醢基) 草醯基二醯肼, N,N' - Double (water hydrazine) thiopropyl hydrazine. 4. Phosphites and phosphonites such as triphenylphosphite, diphenylalkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl) phosphite, trilaurin Phosphite, octadecyl phosphite, distearyl decyl neopentyl diphosphate, tris(2,4-di-t-butylphenyl) phosphite, diisodecyl Neodymidine diphosphite, bis(2,4-di-t-butylphenyl)neopentitol diphosphite, bis(2,4-diisopropylphenylphenyl)neopent 147295 .doc -45- 201100477 Tetraalcohol diphosphite, bis(2,6-di-t-butyl-4-methylphenyl) pentaerythritol-salicin Sa, monoisomethoxy pentane Tetraol di sulphate, bis(2, cardio-second butyl-6-methylphenyl) pentaerythritol diphosphite, bis(2,4,6-tris(t-butylbenzene) Pentaerythritol diphosphite, tristearone sorbitol triphosphite, bismuth (2,4-di-t-butylphenyl) 4,4,-biphenyldiphosphinate , 6-isooctyloxy-2,4,8,10-tetra-t-butyl- 12H-dibenzo[d,g]-l,3,2-dioxaphosphine, double (2, 4_two-third Butyl-6-nonylphenyl)methylphosphite, bis(2,4-di-t-butyl-6-nonylphenyl)ethyl phosphite, 6-fluoro-2,4, 8, l〇-tetra-t-butyl_12_fluorenyl-dibenzo[d,g]_ 1,3,2-dioxaphosphine, 2,2i,2,,_nitro[3 Ethyl tris(3,3,5,5,tetra-dibutyl-1,1'-biphenyl-2,2'-diyl) phosphite], 2-ethylhexyl (3,3' ,5,5'-tetra-t-butyl-1,1,-biphenyl-2,2,-diyl) phosphite, 5-butyl-5-ethyl-2-(2,4,6 - Tri-tert-butylphenoxyl:dioxaphosphol. 5. Amines such as N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctyl By amine, N,N-dilauryl hydroxylamine, ν, Ν-bistetradecylhydroxylamine, hydrazine, hydrazine-bishexadecylhydroxylamine, hydrazine, hydrazine-bis-octadecylhydroxylamine, Ν_hexadecyl Ν Ν Octadecylhydroxylamine, stilbene-ytyl-decyl-octadecylhydroxylamine, hydrazine derived from hydrogenated tallow amine, hydrazine-dialkylhydroxylamine. 6. nitrone 'for example, Ν _ _ _ _ _ phenyl nitro Ketone, Ν_ethyl_α_methyl nitrone, n-octyl-α-heptyl ketone, Ν-lauryl-α-undecyl ketone, Ν-tetradecyl-α-tridecyl nitrate Ketone, Ν_十Base_α_15-denyl nitrone, Ν_octadecyl _ α-heptadecane nitrone, Ν-hexadecyl-α-heptadecysteine, Ν-octadecyl-α-pentadecyl nitrate _,17-kib-α-heptadecylidene, Ν-octadecyl-α-hexadecyl 147295.doc -46- 201100477 nitrone, derived from hydrogenated tallow amine-derived n,n-dialkylhydroxylamine a nitrosylate. 7. A thiosynergist, such as dilauryl thiodipropionate, tetradecyl thiodipropionate, distearyl thiodipropionate or distearyl sulfonate . 8. Peroxide scavengers, such as β-thiodipropionic acid esters (such as lauryl, stearyl, tetradecyl or tridecyl ester), mercaptobenzimidazole or 2-nonylbenzimidazole zinc Salt, dibutyl dithiocarbamate, dioctadecyl disulfide, pentaerythritol ruthenium (Ρ-dodedodecyl) propionate. 0 9. Polylactam stabilizer, for example, a copper salt and a divalent manganese salt in combination with an iodide and/or a phosphorus compound. 10. Alkaline co-stabilizers such as, for example, melamine, polyvinylpyrrolidone, dicyandiamide, tri-propylpropyl cyanuric acid, urea derivatives, spleen derivatives, amines, polyamines Amino sulphate, metal salt of higher carbon number fatty acid and soil test metal salt such as calcium stearate, zinc stearate, tea tree acid town, stearic acid town, sodium linoleate and palmitic acid , tea or catechol. 11. 戚 剂 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Acid and its salts, such as 4_t-butylbenzene f acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such as ionic copolymers Bis(3|,4|-dimethylbenzylidene)Mountain (4), ΐ3·24 — (p-f-diphenylmethylene) sorbitol, philoxine II (stupidyl) mountain (IV) and Irgaclear XT 386 (RTM, Ciba Inc.), 12. Fillers and enhancers' such as calcium carbonate, silicate, fiberglass, 147295.doc •47- 201100477 Glass beads, asbestos, talc, kaolin, mica, barium sulfate, metal Powders or fibers, synthetic fibers of oxides and hydroxides, carbon black, graphite, wood flour and other natural products. 13. Other additives 'such as plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, Fluid control agent, brightener, fire retardant, antistatic agent and foaming agent. Anthranone and chlorenone are disclosed, for example, in U S 4,325,863; US 4,338,244; US 5,175,312; US 5,216,052-US 5,252,643; DE-A-431661 1; DE-A-4316622; DE-A-4316876; -A-0589839 ^ EP-A-0591 102 ; EP-A-1291384 or 3-[4-(2-acetoxyethoxy)phenyl]57-di-t-butylbenzofuran Ketone, 5,7-di-t-butyl _3_[4_(2•stearyloxyethoxy)phenyl]benzof-butan-2-one, 3,3'-double|*5 7-- _Chu--r:aa (4-[2-hydroxyethoxy]phenyl)benzofuran-2-ketone], 5,7-ditriazyl-3-(4-ethoxyl Phenyl)benzopyrene 2_ketone, 3_(4_acetoxy-$-dimethylphenyl)-5,7-di-tert-butylbenzoxan-2-one, 3_(3 ,5_Dimethyl 1 neopentyloxyphenyl)_5,7·di-t-butylbenzobenzoate-2-ketone, 3·(3 4_-methylphenyl)·5,7- Di-t-butylbenzo-c-butyl phenyl...-t-butyl benzo-c-diox-isooctylphenyl)-5-isooctylbenzofuran_2_鲷. Other additives from 0.01 to 10% of the soil are generally used in the weight concentration of the material to be treated. Phenolic Antioxidant of the Agent A preferred composition of the present invention includes as an additional additive, a light stabilizer, and/or a process stabilizer. 147295.doc -48- 201100477 If necessary, incorporate a compound and apply it to the synthetic polymer by known methods (for example, prior to molding or during molding) or by dissolving or dispersing the compound. And other additives are incorporated into the synthetic polymer, if appropriate followed by slow evaporation of the solvent. Another embodiment of the present invention is a method of reducing the surface energy of an organic material, which comprises treating the organic material with at least one formula

Where η is 1,

Ri is hydrogen, CVCh alkyl, C2-C25 alkenyl, -匸〇-115, -〇11(汉10)(:〇-R5 '-C(R10)2C〇-R5 > -CO-N(R6 )-R7 ^ -CH(R10)CO-N(R6)- R7, -c(r10)2CO_n(R6)_R7, _ch(Ri〇)co〇R54_c(r 〇)2C〇_ or5 ; Q when n is At 2 o'clock, R! is unsubstituted or via (:1_(:4 alkyl, benzyl or phenyl substituted Ci_C24 extended alkyl; C2_C24 alkyl, _C〇_R8_C〇_, via oxygen or sulfur) -CH(R10)CO-R8.C〇-CH(R10)- '-C(Ri)2CO-R8-CO-C(R10)2-, -CO-N(R6)-r9_n(r6)- CO-, -ch(r10)co-n(r6)-r9-n(r6)-CO-CH(R10)-, -c(r10)2c〇-N(R6)-R9-N(R6)- CO-C(R10)2-, -CHdfOCO-Oi^-O-CO-CHd.)- or -C(R10)2CO-O-R9-〇-CO- C(Ri〇)2-; when n is 3 hours, 147295.doc • 49· 201100477

R2, r3 and R4 are each independently hydrogen, C!-C25 alkyl, c2-c25 alkenyl,

: with the proviso that at least one of the groups R2, R3 or R4 is -CH(R")-S(0)p-R12; R5 is CVC25 alkyl, c2-c25 alkenyl, unsubstituted or trans heart - phenyl or i-substituted phenyl; or (: 7_(: 12 phenylalkyl, Κ·6 is hydrazine or C1-C4 alkyl, R7 is hydrogen, CVC25 alkyl, unsubstituted or via Ci_c4 a phenyl group substituted by a halogen or a halogen, R8 being an extended or unsubstituted or substituted by a Ci_c4 alkyl group, a benzyl group or a phenyl group - (: 24 alkyl group; a C2_C24 alkyl group which is intervened by oxygen or sulfur , R9 is a direct bond, unsubstituted or C2 to C24 alkyl group substituted by Ci_C4 alkyl, benzyl or phenyl; or C2_CM alkyl extended by oxygen or sulfur,

Rio is hydrogen or CVCs alkyl,

The unit price of a monovalent straight or branched chain organic group of a perfluoroalkyl group having 6 fluorinated carbon atoms, wherein Ri is fluorene, CVC8 alkyl, unsubstituted or substituted by C _C4 alkyl Linear or branched 147295.doc •50- 201100477 R13 is hydrogen, c,-c25 alkyl, c2-c25 alkenyl, _co-r5, -CO-N(R6)-R7 or -ch2-co-n(r6 )-r7, R14 is mouse, Ci-C25 leuco, C2_C25 dilute or -CH(Rii)-S(0)p-Ri2, Rl5 is wind, C1-C25 炫, C2_C25 dilute or -CH (Rii )-S(0)p-Ri2, - R16 is unsubstituted or deuterated-fluorenyl substituted methylene, -s-, -S(O)-, -s(o)2- or -CO -, the ruler is a heart-alkylene group, η is 1, 2 or 3, and Ρ is 0, 1 or 2; and the treatment is carried out in the presence of a compound other than the perfluorinated substituent of formula I. Preferred compounds of the formula I in the process are the same as those of the compositions of the invention. Preferably, the organic material is oil-repellent and water-repellent. A method for imparting oil repellency is preferred. A method of using a compound of formula I, wherein when η is 1,

Ri is nitrogen, CVc12 alkyl, -CO-R5, -C◦-N(R6)-R7 or -CH2-CO- · N(R6)-R7; when η is 2,

Rl is methylene, -co-r8-co- or -CH(R10)-CO-N(R6)-R9-N(R6)-CO-CH(R10)_. When η is 3, 147295. Doc -51 - 201100477

RA 〇 0 , R2 , R3 and R4 are each independently hydrogen, C1-C4 alkyl, -CH(Rii)_S(0)p-Ri2

R..O rm or a R Η ; with the proviso that at least one of the groups &, R3 or R4 is; R 5 is a C1 - C18 alkyl group, Κ·6 is chlorine, R? is hydrogen, C] -C6 alkyl, unsubstituted or substituted by Cl_c4 alkyl,

Re is a phenyl group, and R9 is an ethyl group.

Rio is a scorpion,

Ru is hydrogen, CrC8 alkyl, unsubstituted or methyl substituted phenyl, R12 is _ch2ch2(cf2)5cF3, R13 is chloro or aryl, alkyl, R15 is, R16 is methylene, η Is 1, 2 or 3, and ρ is 0. Other additives may be added before or during the polymerization (or right) before or during the month of crosslinking. The component (b) containing or 147295.doc • 52- 201100477 containing no other additives may be incorporated into the synthetic polymer in pure form or encapsulated in a bad 'W addition component (b) oil or polymer. Component (b) with or without other additives may also be sprayed onto the synthetic polymer. Other additives, such as the conventional additives referred to above, or melts thereof may also be diluted so that they can also be sprayed onto the polymer with such additives. By adding a fusible during the purification of the polymerization catalyst, it can be applied to the mouth using, for example, steam for passivation.

In the case of a spherical polymeric polyolefin, component (b) with or without other additives can be applied, for example, advantageously by mouth coating. The synthetic polymers prepared in this way can be applied in a variety of different forms, such as beads, films, fibers, tapes, molding compositions, as shaped or adhesives for coating materials (especially powder coatings), adhesives, The putty or in particular is a thick layer of polyene (IV) that is in contact with the extraction medium for a long period of time, such as, for example, a tube for liquids, gases, membranes, fibers, low gas barriers, tapes, shaped objects or grooves. A preferred thick layer of a thick hydrocarbon molding has a thickness of β5 〇 _, specifically β 〇 30 mm, for example 2 to 10 mm. The composition according to the invention advantageously (iv) produces a plurality of different shaped articles. Examples are: 1) Floating installations, offshore applications, pontoons, buoys, deck plastic wood, piers, boats, kayaks, paddles and beach reinforcements. 1-2) Automotive applications, specifically bumper, control panel, battery, rear P and 岫4 lining, molded parts under the hood, hat shelf, rear trunk lining, internal residual, airbag Cover, electronic mold for accessories (lights) 4 Do not look at the window glass of the control panel, headlight glass, instrument panel, 147295.doc •53- 201100477 Exterior lining, bedding, car lights, headlights, parking lights, Rear lights, brake lights, interior and exterior trim, door panels, oil sump, broken glass front 岣 _ S1de), rear window, seat back, outer panel, wire insulation, shaped extrusion for seals, Sheath, pillar cover, chassis part, exhaust system, fuel transition / filler, fuel fruit, oil _, anti-scratch strip, folding roof, exterior mirror, exterior parts, fasteners / fixing Objects, front end modules, glass, hinges, lock systems, luggage/roof frames, compression/stamping parts, seals, side impact protection, silencers/sounders and skylights. 1-3) Road traffic devices' signs of Xiao Dingyan, poles for road marking, auto parts, warning triangles, ® kits, helmets, tires. 1-4) Devices for aircraft, railways, motor vehicles (automobiles, motorcycles), including decorations. Μ) Devices used in space applications, specifically rockets and satellites such as returning to the baffle. [-6] For construction and design, mining applications, quiet systems, street security islands and shelters. π 1) Appliances, enclosures and coverings for general and electrical/electronic devices (personal computers, telephones, cell phones, printer televisions, audio and video equipment), flower pots, satellite τν bowls and panel equipment. H-2) Sheaths for other materials such as steel or fabric. Π-3) Devices for the electronics industry, in particular sockets, especially for computer sockets, for electrical/electronic components, printed circuit board enclosures and materials for electronic data storage (such as chips, check cards) Or credit card. Π_4) Electric appliance, specifically washing machine, drum, oven (microwave oven), 147295.doc •54- 201100477 Dishwasher, mixer and bucket. II- 5) Lampshades (eg street lamps, lampshades). Π-6) Applications in wires and wires (semiconductors, insulators and electric sleeving). Π-7) Foil for condensers, refrigerators, heating units, air conditioners, electronic packages, semiconductors, coffee machines, and vacuum cleaners. ΠΙ-1) Technical objects such as gears (gears), sliding fittings, spacers, screws 'nuts, handles and knobs. III-2) Rotor blades' ventilators and windmill blades, solar installations, swimming pools, swimming pool covers, pool linings, ponds, bridges, garments, partitions, troughs, folding walls, roofs, shadings (eg Blinds, fittings, fittings between pipes, casings and conveyor belts. ΪΙΙ-3) Cleaning items, specifically the shower room, toilet seat, and cover groove. ΙΠ-4) Hygiene products, specific diapers (baby, adult deafness, distressed feminine hygiene products, shower curtains, brushes, mats, bathing rainbows, mobile shoulders, toothbrushes and potty. III-5) for water , waste water and chemical tubes (crosslinked or uncrosslinked), tubes for wire or cable protection, tubes for gas, oil and dirt, drains 'downflow pipes and drainage systems. III-6) Shapes of any geometry (window) and side lines. HI-7) Breaking substitutes, specifically extrusion plates, for construction (single, double or multi-layer), aircraft, school, glass for extrusion panels, for building glass and, trains, traffic, cleaning Object and window film in the greenhouse. 147295.doc -55- 201100477 ΙΙί-8) Plate (wall, cutting board), extrusion coating (photo paper, tetrapack and tube coating), storage bin, wood substitute, plastic wood, wood Composites, walls, surfaces, furniture, decorative foils, floor coverings (internal and external applications), flooring, fenders and tiles. III-9) Inhalation and elimination of manifolds. IH-10) Cement-, concrete-, composite-application and cover, side line and jacket, barrier, handrail, kitchen countertop, roof, roof slab, floor tile and water-repellent cloth. W-i) panels (walls, cutting panels), pallets, artificial turf, artificial turf, man-made coverings for stadium rings (sports), artificial flooring and belts for stadium rings (promotional sports). IV-2) woven fabric continuous and short fibers (carpet/hygiene/geotextile monofilament; transitioner; rag/curtain (shading)/medical application), loose fiber (such as gown/protective clothing), net Shape, weaving, I-line, string, rope, thin line, seat belt, clothes, underwear, gloves; L close-fitting clothes, clothing, swimwear, sportswear, raincoats (sun umbrellas, sunshades), parachutes, hang gliding, Sails, "balloon silk", camping supplies, tents, inflatable beds, sunbeds, space bags and bags. IV-3) For roofs, walkways, garbage dumps, ponds, garbage dumps, gallbladder walls, roofing membranes, low air permeability barriers, swimming pools, curtains (shading)/shading, awnings, covering paper, food packaging and Package (flexible and solid), medical packaging (flexible and solid), airbags/belts, armrests and headrests, carpets, center console, control panel' drive, door panel, rut , door trim, roof shed, interior lighting, interior rearview mirror,; 147295.doc -56- 201100477 The film of the wood, the rear lid, the seat, the steering column, the steering wheel, the fabric and the rear compartment trim, Insulators, covers and seals v) Membrane (packaging, landfill, lamination, agriculture and horticulture, greenhouse 'roots, mulch, silage), bundled packaging, swimming pool, garbage bags, wallpaper, stretch film, wine Coconut, desalting membrane, battery and connector. VI-1) Food packaging and packaging (pullable and solid), bottles. ❹ VI-2) Storage systems such as boxes (crate), trunks, plants, household boxes, pallets, shelves, rails, screw boxes, parcels and cans. VI_3) Ink E, syringe, medical application, container for any transportation, garbage bin and garbage bin, garbage bag, box, wire barrel, garbage plastic bag, wheeled trash can, general container, used for water, used Water/chemical/gas/oil/gasoline/diesel tanks; tank linings, boxes, crates, battery boxes, sinks, medical devices such as pistons, (iv) packaging applications, reading devices and pharmaceuticals) extrusion coating (photo paper, Tetra Pak, tube coating), any type of equipment (such as electrical appliances, thermos / hangers), solids such as sockets, wires and cable clamps, zippers, closures, locks, buckle snaps . Such as sports ^ objects and fitness equipment, sports mats, ski boots, straight and cake skates, skis, feet, sports surfaces (such as tennis courts); spiral moss, (4) 1, line Xiao in bottles and cans I based. VII-3) General furniture, foaming items (, 士^, to shock absorbers), foam, sponge, dish cloth, 塾, park chair, stadium seat, Zhuo, sofa, toy, assembly kit (board / graphics / ball), drama, ) % of the show, slides and games 147295.doc • 57- 201100477 car. VII-4) Materials used for optical and magnetic data storage. VII-5) Kitchenware (eat, drink, cook, store). VII_6) for CD, kakun and video cassettes; any type of office supplies (ballpoint pens, stamps and stamps, pick-ups, plates, tracks), any volume and capacity (beverage, detergent; package: two Cosmetics) bottles and ray belts. Vn-7) shoes (shoes/sole), insoles, materials, adhesives, food boxes (fruit, vegetables, shaw,, fun, and) synthetic paper, bottle labels, sofas, artificial joints (human), printing Board (diligence), printed circuit board and display technology. VII-8) Filled polymer (talc, chalk, soil (kaolin), Shishi limestone pigment, stone anti-black, Ti〇2, mica, nanocomposite, dolomite, agglomerate, glass, asbestos ) device. The sensation/interest includes the non-woven medical fiber and related clothing (surgical gown, belly cloth, bandage), construction fabric (home coating, roof, swimming pool coating) as component (a) A combination of fibers and fabrics in furniture (carpet, dish cloth, shower curtain). Of particular interest are the compositions comprising fibers and nonwovens as component (a). Another embodiment of the invention is directed to a shaped article, specific. The fibers and nonwovens of particular interest are included in the films, tubes, styling, bottles, tanks or container fibers of the compositions described above.老日日ώ 为 - is an embodiment relating to a molding comprising the above composition 147295.doc -58- 201100477 Rotary molded part. The molded object is specific to the ancient 筏, the office & the mountain. <The effect of injection, blow molding, compression or gel forming or extrusion molding. The present invention, which is also a preferred embodiment, is used as a reducing agent in the surface b of an organic material, such as [exhaust oil reagent and water repellent reagent]. Preferably, the compound of the formula I or the component (8) and the other additives as needed are used as a reducing agent for the surface energy of the organic material [for example, an increase in oil repellency and water repellency! The objects mentioned are the same. The following examples illustrate the invention: parts or percentages are related to weight 0 Example 1: Compound 101 (2·methyl_4,6_double_(3,3,4,4,5,5,6, Preparation of 6,7,7,88,8-tridecafluoro-octylsulfonylmethyl)phenol

F F F F F F

10.6 g (98·0 mm〇i) of o-nonylphenol, 74.6 g (196 mmol) of 1H, 1H, 2H, 2H-perfluorooctane-thiol, 2.70 g (19.6 mmol) of dimethyl The amine (330/〇 in EtOH), 11.8 g (392 mmol) of trioxane and 1.0 ml of N,N-dimethylformamide (Dmf) were mixed and heated under reflux for 4 hours under nitrogen atmosphere. . Ethyl acetate was added and the organic phase was washed repeatedly with water and brine until the pH was neutral. The organic phase was dried over magnesium sulfate, filtered and concentrated using a vacuum rotary evaporator to afford <RTIgt;</RTI> NMR: (400 MHz, CDC13): δ = 147295.doc -59- 201100477 7.06 (d, J = 1.6 Hz, ArH, 1H); 6.92 (d, J = 1.6 Hz, ArH, 1H); 6.06 (s, OH, 1H); 3.83 (s, ArCH2, 2H); 3.66 (s, ArCH2, 2H); 2.70-2.55 (m, C//2CH2CF25 4H); 2.40-2.20 (m, CHA/^CFh 4H); (s, CH3, 3H). Example 2: Compound 102 (2-tert-butyl-4,6-bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-trifluoro) Preparation of octylsulfonylmethyl) phenol

F F F F F F

FFFFFF gives 0.80 g (5.35 mmol) of 2-tert-butyl-pan, 6.51 g (17.1 mmol) of 1H,1H,2H,2H-perfluorooctane _ι_thiol, 〇22 g (1.61) Ment) of dimethylamine (3 3% in EtOH), 0.96 g (32.1 mmol) of trioxane and 1.0 m of N,N-dimethylformamide (Dmf) mixed and refluxed It was heated under a nitrogen atmosphere for 12 hours. Ethyl acetate was added and the organic phase was washed repeatedly with water and brine until the pH was neutral. The organic phase was dried over MgSO.sub.4, filtered and concentrated on vacuo. The crude product (cyclohexane / ethyl acetate: 4 EtOAc: EtOAc) (:4 NMR: (400 MHz, CDC13): δ = 7.18 (d, J = 2.0 Hz, ArH, 1H); 6.95 (d, J = 2.0 Hz, ArH, 1H); 6.58 (s, OH, 1H ); 3.87 (s, ArCH2, 2H); 3.68 (s, ArCH2, 2H); 2.65-2.55 (m,

Ci/2CH2CF25 4H); 2.40-2.15 (m, CH2CH2CF2, 4H); 1.43 (s, CH3, 9H). 147295.doc •60- 201100477 Example 3: Compound 103 (2,4,6_three_(3,3,4,4,5 5,6 6,7,7,8,8,8-tri-trifluoro- Preparation of octylsulfonylmethyl) phenol

Tli44+p F F F

(103) 〇·37 g (3.93 mmol) of the desired, 4.79 g (12.6 mmol) of 1H,1H,2H,2H- Ο Ο perfluorooctane-1-thiol, 〇.l6 g (1.18 mm〇 1) didecylamine (33% in EtOH), 〇71 g (23.6 mm〇l) of trimeric ruthenium and 1〇m^N N-dimercaptodecylamine (DMF) mixed and It was heated under reflux for 12 hours under a nitrogen atmosphere. Ethyl acetate was added and the organic phase was washed repeatedly with water and brine until the pH was neutral. The organic phase was dried over MgSO.sub.4, filtered and evaporated. The crude product (cyclohexyl/acetic acid ethyl acetate: 19:1) was purified by flash chromatography to afford 3,85 (d) compound 103 ' pale yellow solids ' m.p. 36-40. (:. towel NMR: (300 ΜΗζ, CDC13): δ = 7.10 (s, ArH, 2H); 6.82 (s, OH, 1H); 3.84 (s^ ArCH2, 4H); 3.67 (s, ArCH2> 2H) ; 2.70-2.55 (m, C^2CH2CF2! 6H); 2.50-2.15 (m, CH2Ci^2CF2, 6H). 2' Example 4: Compound 104 (terephthalic acid double _[2_methyl_4,6 Preparation of _double_(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octylsulfonylmethyl)-phenyl ester) 147295.doc -61· 201100477

87.5 g (98.0 mmol) of the compound ιοί and 11 · 9 g (i 18 mmol) of triethylamine were dissolved in 200 ml of tetrahydrofuran. 9.95 g (49.0 mmol) of p-benzoquinone gas was added portionwise to the reaction mixture at room temperature under a nitrogen atmosphere, and the reaction mixture was stirred at room temperature for 12 hr. Ethyl acetate (200 ml) was added and the organic phase was washed repeatedly with water until the pH was neutral. The organic phase was dried over MgSO.sub.4, filtered and concentrated on a vacuum rotary evaporator to afford 93.2 g of pale yellow wax. The crude product was suspended in decyl alcohol (200 ml), heated to reflux and filtered. The filtered solid was then crystallized from hexanes (400 ml) to afford 50.1 g of Compound 104 as a white solid, m.p. !H NMR: (400 MHz, CDC13): δ = 8.40 (s, ArH, 4H); 7.25-7.15 (m, ArH, 4H); 3.76 (s, ArCH2, 4H); 3.69 (s, ArCH2, 4H) ; 2.75-2.60 (m, C/f2CH2CF2, 8H); 2.45-2.15 (m, CH2C//2CF2, 8H); 2.23 (s, CH3, 6H). Example 5: Compound 105 (terephthalic acid bis-[2,4,6-tri-(3,3,4,4,5,5, 6,6,7,7,8,8,8-ten Preparation of trifluoro-octylsulfonylmethyl)-phenyl] ester 147295.doc -62· 201100477

4.80 g (3·78 mmol) of compound ι〇3 and 0 42 g (4.16 mmol) of triethylamine were dissolved in 100 ml of tetrahydrofuran. 0.38 g (1.89 mmol) of terephthalic acid chloride was added portionwise to the reaction mixture at 5 ° C and a nitrogen atmosphere. The reaction mixture was stirred at 50 ° C for 12 hours. Ethyl acetate (100 ml) was added and the organic phase was washed repeatedly with water until the pH was neutral. The organic phase was dried over MgSO.sub.4, filtered and concentrated on vacuo. The crude product was crystallized from B.sub.4 (5 〇 </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; (s, ArCH2, 12H); 2.40-2.05 (m, 96 〇C. H NMR: (400 MHz, CDC13): δ 7.30 (s, ArH, 4H); 3.70 (s, ArCH2, ' 8H); 2.50 (m, C/i2CH2CF2, 1 CH2Ci/2CF2, 12H). (^^2,4,6--(3,3,4,4,5,5,6,6,7,7,8,8 Preparation of 8,8-trifluoro-octylsulfonylmethyl)-phenyl ester 147295.doc -63· 201100477

1.50 g (l.18 mmol) of compound i〇3 and 0.14 g (l.42 mmol) of triethylamine were dissolved in 20 ml of tetrahydrofuran. 0.09 g (1.88 mmol) of acetamidine chloride was added to the reaction mixture at room temperature under a nitrogen atmosphere. The reaction mixture was searched for 4 hours at room temperature. Add ethyl acetate ($ 〇 m 1) and rinse the organic phase repeatedly with water until the pH is neutral. The organic phase was dried over magnesium sulfate, filtered and concentrated using a vacuum rotary evaporator to afford a pale brown color of 1-5 g. The crude product was crystallized from acetonitrile / water (20 ml / 60 ml). 4 NMR: (300 MHz, CDC13): δ = 7.30 (s,

ArH, 2H); 3.73 (s, ArCH2, 2H); 3.65 (s, ArCH2, 4H); 2.70- 2-55 (m, C//2CH2CF2, 6H); 2.45-2.15 (m, CH2C^2CF2, 6H 2-38 (s, COCH3, 3H) 〇 Example 7: Water repellency and oil repellency in polypropylene The repellency of the compound of formula I was determined and tested according to the following procedure. The preparation is a polypropylene nonwoven and a heat treatment (for example, a combination of 130% (the next 1 minute) which promotes the migration of the additive to the surface and the proper surface rearrangement of the chemical groups. This additional thermal cycle is recommended. The compound of formula I was melted to obtain a uniform redistribution on the surface of the substrate. An industrial sample of a polypropylene nonwoven having a fiber weight of 4 〇g/m 2 was impregnated in 1% of the test compound in an isopropanol solution. Simultaneous application of ultrasonic energy - minutes. After that, samples of 147295.doc -64 - 201100477 were dried overnight at room temperature, and then allowed to dry in an oven for two hours at 90 ° C. Then some samples were made at 130 °. Annealing for 10 minutes at C. Treated nonwoven samples were evaluated in a water repellency test similar to INDA Test Method 80.8 (99). The wetting behavior of the nonwovens was tested with a series of water/isopropanol mixtures. Behavioral observations were graded from 0 (water wet, no water repellency) to 1 〇 (optimal water repellency). The results are summarized in Table 1. • Treated nonwoven samples are similar to AATCC test methods 11 8- 〇 1997/ISO 1441 Evaluation was carried out in the oil repellency test method of 9. This test was carried out in accordance with the same concept as described in the water repellency test method, but a series of hydrocarbons were used as the test solvent. The observation of the wet behavior was carried out by 〇 (non-oil discharge) to 8 ( The best oil repellency). The results are summarized in Table 2. Table 1: Water repellency of the original sample of the example compound Water repellency after annealing 7a Compound 104 9 10 7b Compound 105 10 10 7c Compound 106 7 7 Table 2: Examples Oil repellency of the original sample of the compound. Oil repellency after annealing. Compound 104 4 5 7e Compound 105 6 6 147295.doc -65·

Claims (1)

201100477 VII. Scope of application: 1. A composition comprising a) an organic material susceptible to degradation by oxidation, heat or light, and b) a compound of formula I, (I) where, ο When η is 1, Ri is hydrogen, CVC25 alkyl, C2-C25 alkenyl, -(:0-115, -(:11(111())(30-R5 ' -C(R10)2CO-R5 ^ -CO-N(R6)-R7 ' -CH(R10)CO-N(R6)- r7, -c(r10)2co-n(r6)-r7, -ch(r10)coor5 or -c(r10 2co-or5 ; when n is 2, R! is unsubstituted or substituted by alkyl-, benzyl or phenyl-substituted alkyl; c2-c24 alkyl, via oxygen or sulfur, -CO-R8-CO-, -CH(R10)CO-R8-CO-CH(R10)- '-C(R10)2CO-R8-CO-C(R10)2-' -CO-N(R6) -R9-N(R6)-CO- &gt; -CH(R,〇)CO-N(R6)-R9-N(R6)-CO-CH(R10)- ^ -C(R10)2CO-N( R6)-R9-N(R6)-CO-C(R10)2-, -ch(r10)co-o-r9-o-co-ch(r10)- or -c(r10)2co-o-r9 - O-CO-C(R10)2-; When n is 3, R1 is ο ο 147295.doc 201100477 R2, I and R4 are each independently nitrogen, 'alkyl, C2-C25 alkenyl, 14 Η R Η 0R13 or •CH(R]丨)-S(0)p-R12, ___ 13 ' R R R3 '15 〇 Rl3 仁 with the condition that at least one of the groups R2, R3 or R4 is + · R5 is Ci-C25 炫, c2-c25 is suspected to be + _ ^, benzyl, unsubstituted or C丨-C4 alkyl or halogen substituted phenyl; or Cr #β 丨2 stylalkyl, R&gt;6 is wind or C 1 -C4 alkyl, R·7 is hydrazine, Ci-C25 alkyl, Take ^^ γ Λ&gt; ', 代 or, · star C丨-c4 alkyl or halogen substituted phenyl, ~ is phenyl, unsubstituted or substituted by W or 1 phenyl or 4 a base; an oxygen or sulfur intervening W, an alkyl group, R9 is a direct bond; an unsubstituted or C-based, a phenyl-substituted CrC:24 alkyl group: or an oxygen or sulfur interstitial C2 Heart alkyl, Rio is hydrogen or C-C8 alkyl, R&quot; is hydrogen, Cl-c-based, unsubstituted or Ci_M-based substituent, the core contains all 6 perfluorocarbon atoms a monovalent or branched organic group of a fluoroalkyl group, N(R6)-R7 or -CH2-CO-N(R6)-R, Rn is hydrogen, Cl-c25 alkyl, C2_C25 alkenyl, _c〇_R5, 147295.doc 2- 201100477 R14 is chlorine, Ci_c25 alkyl, C2_C25 alkenyl or -CH(Rn)_s(0)p_ R1 2, R15 is hydrogen, Ci_C25 alkyl, C2_c25 alkenyl or ·εΗ(Κιι)·3(0)ρ_ R12, Rl6 is unsubstituted or trans-salt-substituted methylene, -s-, - s(0)-, -S(〇)2- or, Ο Rl7 is a Ci-C4 alkyl group, n is 1, 2 or 3, and Ρ is 〇, 1 or 2; but with the proviso that it does not include Α and Compound of hydrazine; Wherein the compound does not comprise a compound containing a perfluorinated substituent other than formula (I). G 2. The composition of claim 1, wherein when η is 1, R1 is hydrogen, Cl_Ci8 alkyl, C2-C18 alkenyl, -CO-R5, ·&lt;:ο-ν(ιι6)-R7 or -CH2-C〇-N(R6)-R7 ; When η is 2, R! is unsubstituted or Ci_Ci8 substituted by (1:(_:4 alkyl, benzyl or phenyl); Oxygen or sulfur interstitial C2_Ci8 alkyl, _c〇_R8_c〇_, -c〇-n(r6)-r9_n(R6)_c〇 or _CH(Ri〇) c〇n(R6) R9_n(R6)_ 147295.doc 201100477 CO-CH(R,〇)-; Ri is When n is 3, R2, R3 and R4 are each independently hydrogen, Cl_C18 alkyl, C2-C-8 alkenyl, However, the condition is that at least one of the group R2, the core or the rule 4 is _CH(Rii), S(0)p-Ri2; R·5 is a CVCu alkyl group, a CyCi8 alkenyl group, an unsubstituted or a C1-C4 burned. a phenyl substituted with a base or a peptidin; or a C7_Ci2 phenylalkyl group, R6 is hydrogen or a Ci-C4 alkyl group, R7 is hydrogen, C]-C is aralkyl, unsubstituted or substituted by Ci_C4 alkyl or halogen Phenyl, RS is extended, unsubstituted or substituted by Ci_C4 alkyl, benzyl or phenyl (:!-(:24 extended alkyl; via oxygen or sulfur Rs» as a direct bond or not Substituted or substituted by C 2-(:18 alkyl, Rio is hydrogen or CVC8 alkyl, Rn is hydrogen, (^-(:8 alkyl, C2-C24 extended alkyl without oxygen or sulfur) , L substituted or substituted by (: 1-〇4 alkyl, benzyl or phenyl substituted unsubstituted or substituted by c,-c4 alkyl 147295.doc 201100477 base, Ru is composed of having 6 perfluorocarbons A monovalent linear or branched organic group of a perfluoroalkyl group of an atom, 13 being hydrogen, a Ci-Ci8 alkyl group, a C2-C18 dilute group, _c〇-R5, _c〇_N (R0-R7 or -CH2_CO- N(R6)-R7, Rl4 is hydrogen, C1_C18 alkyl, C2-C18 alkenyl or _CH(Rl〇_s(9)p_Rl2, 〇R15 is hydrogen, Cl-Cl8 alkyl, C2-C18 alkenyl or _CH(R&quot;)-S(0)p-R12, 16 is unsubstituted or substituted with Ci_C4 alkyl, _s_, _s(〇)_, -s(〇)2- or -c〇-, Han" is a heart-匕 alkyl group, η is 1, 2 or 3, and ρ is 0, 1 or 2. 3· as requested a composition of 1 or 2 wherein it is saturated and comprises an atom, wherein 6 carbon atoms are fully fluorinated and comprise at least one terminal fluorenyl group. The composition of the term 1 or 2, wherein Ri2 is _CH2CH^CF^CF3. 5. The composition of claim 1 or 2, wherein, when η is 1, 1 is hydrogen, (: 丨-(:18 alkyl '-c〇_R5, _c 〇n(R6) R7 or _CH2· C〇-N(R6)-r7 ; When η is 2, Rl is Ci-C8 stretching base-CO-R8-C〇- ^ -CO-N(R6) -R9-N(R6). 147295.doc 201100477 CO- or -CH(R)〇-CO-N(R6)-R9-N(R6)-CO-CH(R10)-; When n is 3 , ο ο Ri is r2, r3 and R4 are each independently hydrogen, Cl_c8 alkyl, _CH(R&quot;) R130, , R14 HR. ;P R12,——R 16 H or a R H R 16 HR or13; but with the proviso that at least one of the groups 15 15 R2, R3 or R4 is -ch(ru)-s(o)p-r12; alkyl, unsubstituted or via (:1-(: 4-alkyl-substituted phenyl; or benzyl, Κ·6 is hydrogen, unsubstituted or substituted by Ci-C4 alkyl benzene R7 is hydrogen, CVCs alkyl, aryl, R·8 is phenyl or C ^-Cw stretching base, Rs» is 〇2-€118 stretching base, Rh^CVC^ alkyl, R" is hydrogen, Ci-Cs alkyl, unsubstituted or stupidized by hydrazine Ri2 is -ch2ch2(cf2)5cf3, R13 is hydrogen or -CO-R5, R14 is hydrogen or Ci-Cs alkyl, alkyl or -CHdd-SCOVRu, Ri6 is methylene, η is 1, 2 or 3, and 147295.doc 201100477 p is 0. 6. A composition according to claim 1 or 2, a synthetic or synthetic polymer. 7. A composition according to claim 1 or 2. 8. If claim 1 or 2 The composition, the composition, wherein the organic material is natural, and the organic material is a synthetic polymerization wherein the organic material is a fiber or a non-woven fabric. 9. The composition of claim 2 or 2, wherein the compound is 0.01 to 10 by weight of the organic material The amount of % is present. The composition of claim 1 or 2 additionally comprising other additives than the organic material and the compound of formula I. 11. The composition of claim 1 or 2, which includes a phenolic antioxidant, a light stabilizer, and/or a processing stabilizer for other additives. 12. A method of reducing surface energy of an organic material, comprising treating the organic material with at least one compound of formula I, Wherein, when η is 1, Ri is hydrogen, CVC25 alkyl, c2-C25 alkenyl, _c〇-R5, -CH(R10)CO-R5 '-C(R10)2C〇-R5 . -CO-N (R6).R7 . -CH(R10)CO-N(R6)-R7 ' -C(R,〇)2C〇-N(R6)-R7 &gt; -CH(R10)C〇〇R5 ^ -C (R10)2C〇. or5 ; 147295.doc 201100477 When η is 2, Ri is a Ci-C24 alkyl group which is unsubstituted or substituted by a C1-C4 alkyl group, a benzyl group or a phenyl group; C2-C24 alkyl, -CO-R8-CO-, -CH(R10)CO-R8-CO-CH(R10)- '-C(R10)2CO-R8-CO-C(R10)2- , -CO-N(R6)-R9_N(R6)-CO-, -CH(Ri〇)CO-N(R6)-R9_N(R6)-CO-CH(R10)- '-C(R10)2CO- N(R6)-R9-N(R6)-CO-C(R10)2-, -CH(Ri〇)CO-0-R9-0-CO-CH(Ri〇)- or -C(Ri〇) 2CO-0-R9-〇C 〇- C ( R10) 2 -, when n is 3, R_2, R3 and Κ·4 are independent of each other as nitrogen, C1-C25 alkyl, C2-C25 thin 15 R13O, ,R14 Η Η R base, -CP^Ry-SCCOp-Ru, one r However, it is a proviso that at least one of the groups R2, R3 or R4 is -CHdO-SCCOp-Rn; {^ is ^-匚25 alkyl, C2-C25 alkenyl, unsubstituted or hydrazine--alkyl Or halogen substituted phenyl; or c7-c12 phenylalkyl, R6 is hydrogen or CVC4 alkyl, R7 is hydrogen, C^-Cw alkyl, unsubstituted or via (^-(:4 alkyl or halogen) Substituted phenyl, 147295.doc 201100477 R8 is phenyl, unsubstituted or substituted with s-alkenyl, benzyl or phenyl <^-(:24 alkyl; via oxygen or sulfur C2_C24 alkylene, a direct bond, unsubstituted or C2_C24 alkyl substituted by Ci_C4 alkyl, benzyl or phenyl; or c2-c24 alkyl by oxygen or sulfur, . ^-Cs, Rii is hydrogen, C^-C: 8 fen, unsubstituted or substituted with Ci_c4 alkyl, 0 R12 is a perfluoroalkyl group containing 6 perfluorocarbon atoms Monovalent linear or branched organic group, Rl3 is hydrogen, CU-C25, C2_C25 alkenyl, -CO-R5, -CO-called 6)-117 or -&lt;:&amp;-(:0- :^(116)-117, ^ R&quot; is hydrogen, CVC25 alkyl, C2-C25 alkenyl or -CH(R&quot;)-S(0)p - R12, Ri5 is hydrogen, CVC25 leumino, C2-C25 alkenyl or -CHdd-SCCOp-R12, Q Ri6 is sub-f*, _s-, -s(o) unsubstituted or substituted with fluorenyl-fluorenyl )-, _8(0)2_ or -.0_, R1 7 is a C 1 - C 4 alkyl group, η is 1, 2 or 3, -, ρ is 0, 1 or 2; and the processing system is nothing more than The method of claim 12, wherein the method of claim 12, wherein η is 1, 147295.doc 201100477 R! is hydrogen, CVCu alkyl, _c0_r5, -CO-N(R6)-R74-CH2-CO-N(R6)-r7 ; When n is 2, Ri is methylene, -CO-R8_CO_ or _CH(R10)-CO-N (R6 )-R9-N(R6)-CO-CH(R10)- ; When η is 3, R! is ύ R2, R3&amp;r4 are independently of each other hydrogen, Ci_c4 alkyl, -CH(Rii)_s(0)p· R13°v /R14 Rl2 or —R Η · 16 Η R but with the condition that the group r2, r3 or r4 to 15 is less than -CH(Rn)-S(〇)p-Rl2; alkyl, ruler 6 is gas, h is hydrogen, CrCe Alkyl, unsubstituted or phenyl substituted by {1{4 alkyl, R8 is phenyl, R.9 is ethyl, R10 is fluorenyl, R&quot; is hydrogen, CVCs alkyl, without Ri2 Is -CH2CH2(CF2)5CF3, substituted or methyl substituted phenyl, R13 is chloro or aryl, Rule 14 is Ci-C4 alkyl, 147295.doc -10- 201100477 Rl6 is an anthracenylene group, η is 1, 2 or 3, and ρ is 0. Material Discharge Surface Energy 14. The method and water repellency of claim 12 or 13. ^ A use of a compound of the formula 请求 as an organic reducing agent. 〇 147295.doc -11- 201100477 IV. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the best display. Chemical formula of the inventive feature: 〇 H R4 (I) 147295.doc